Annapolis

Showing

$800

Book

Beautifully water front Contemporary Home in Bay R

Annapolis house
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill. Once you see the view from…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful Family House!

Left on Oct 17, 2013 for a stay in August 2013

We were fortunate to stay in this lovely home over Plebe Parent Weekend. It was perfect for our family of 6. There was plenty of room to spread out or come together for family time. The large dining table made us feel right at home. The bedding was fresh with new linens and towels in all the rooms. We enjoyed the lovely water views and great location. The Bay Ridge house is a short ride to the …

$150

Book

1 bedroom cottage near water, dog friendly

North Beach cottage – 19.0 mi away
1 BR / 1 BA / Sleeps 5 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full kitchen, and a backyard …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Quiet and peaceful!

Left on Sep 26, 2011 for a stay in September 2011

We had a very nice stay at Seahorse cottage. It was on a quiet street, but only a short walk to the boardwalk. The owners are wonderful to talk to. We hope to go back next year for our anniversary.

$250

Book

Charming Vintage Cottage/secluded Yard/Walk. WIFI

Annapolis cottage
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks from Spa Creek. This…
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great place. My dog loved the yard. I loved the Porch

Left on Jul 15, 2014 for a stay in December 2013

If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to grill a couple a steaks and have a semi barbeque (little cold so the porch was perfect) by eating and entertaining on the Porch.

$375

Book

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Saint Michaels house – 20.0 mi away
4 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and furnished for a comfortable …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect weekend getaway!

Left on Jan 10, 2014 for a stay in December 2013

My family recently spent a memorable weekend in December at Sandy Pines. We comfortably shared the house with a group of friends -- three other couples and their young children. The house has a lovely home-away-from-home feel. We especially enjoyed the wood-burning fireplace in the evenings.
Sandy Pines is perfectly situated -- a short drive from St. Michaels, and on a tranquil spot by the Bay…

Renovated Luxury Waterview House - North Beach vacation rentals
1 / 9

$250

Book

Renovated Luxury Waterview House

North Beach house – 18.5 mi away
3 BR / 2 BA / Sleeps 6 | Quick view

Details

This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to beach, boardwalk, …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

$280

Inquire

Peaceful, Waterfront Home w/Pier on Kent Island

Chester house – 10.5 mi away
4 BR / 2 BA / Sleeps 8 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The location is serene on a 3 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Unbelievable value

Left on Nov 04, 2010 for a stay in May 2010

We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we…

1 / 25

$490

Book

Upscale House/12 MINUTES FROM DC

Bowie house – 18.2 mi away
5 BR / 3 BA / Sleeps 13 | Quick view

Details

Beautiful, comfortable single-family house located in the exclusif and upscale dunbarton community. Easy access to many attractions including Six Flags, HurrIcane Harbor, golf courses, walking paths, Forest PARK national preserve, the redskins FEDEX FIELD, historicDC, FAMOUS MAGIC JOHNSON'S BOULEVARD( RESTAURANTS, …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

$350

Inquire

Love Point Waterfront

Kent Island house – 10.9 mi away
3 BR / 2 BA / Sleeps 12 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Located on the Eastern shore of Maryland, Kent Island is a small area 13 miles long and 5 miles wide. The Bay Bridge spans the Cheasapeake bay from the Western shore to Kent Island. We are 4.5 miles north of the bridge in a charming old waterfront community called Love Point! Love Point is quiet area of single …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(4)

Home away from Home , We feel the weight of the world disappear when we walk through the door.

Left on Apr 17, 2015 for a stay in April 2015

Paula's Bay House is home away from home. like visiting the vacation house your family has had for years. You have a wall of windows view of the water. We spend hours just watching the birds and the waves. At night we stoke up the fire and gaze at the flickering flames and just be in the moment of quiet and peaceful relaxation. This house is warm and eclectic , has all the modern conveniences…

$425

Book

Beautiful Murray Hill Home (Annapolis)

Annapolis house
4 BR / 3 BA / Sleeps 9 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking attention to detail to …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Comfortable and secure in a great home - almost as good as at ho

Left on Nov 03, 2013 for a stay in October 2013

The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town.

We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies.

We certainly will attempt…

$250

Book

* 3 Bedroom Rental House in Historic Rock Hall MD

Rock Hall house – 17.5 mi away
3 BR / 2 BA / Sleeps 7 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s Crab House, The …
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

Excellent Value in a Great Location

Left on Apr 18, 2012 for a stay in May 2011

We have rented this home on several occasions over the past few years, and always found everything clean and in good working order. The large back yard is great for activities with our grandkids. Easy walking distance to Watermen's Restaurant and The Harbour Shack is a real bonus. Highly recommended!

$750

Book

Charming and Spacious Annapolis Victorian

Annapolis house
6 BR / 5 BA / Sleeps 13 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms include a pool table …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Charming house in a great location! Perfect for larger group!

Left on Aug 11, 2014 for a stay in August 2014

We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large deck out back and patio furniture were wonderful for grilling and eating dinner outside. (The outdoor giant Jenga was a hit!) We went with a group of various couples and a couple of our single friends and everyone had …

$190

Inquire

Premier Cottage in St. Michaels- In Town Location!

Saint Michaels house – 19.8 mi away
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the…
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

I will never go back to the Jersey Shore Again!!!

Left on Aug 18, 2014 for a stay in August 2014

Location location location!

Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!

$350

Inquire

Large Historic Home On Harbor in St. Michaels

Saint Michaels house – 19.8 mi away
7 BR / 4 BA / Sleeps 11 | Quick view
Excellent6 Reviews

Details

Reviews

(6)

The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and shops in St. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(6)

This was the perfect home for a week of wedding planning and family relaxation time.

Left on Jul 23, 2014 for a stay in June 2014

Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time together finalizing wedding plans. The stay at the Harrison Home added so many memories to the already fond memories of a wedding. We cooked together with all the amenities in the kitchen. The home was so large we could …

1 / 11

$209

Book

Love Point Bay Vacation Home

Stevensville condo – 10.8 mi away
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave your worries behind …
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask
1 / 23

$250

Inquire

TreeHouse

Annapolis house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped.
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 9

$300

Book

2. Private 20 acre waterfront estate - studio apt

Annapolis condo
1 BR / 1 BA / Sleeps 2 | Quick view

Details

This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as the architect - …
  • Pet friendly - ask
  • Suitable for the elderly
  • Wheelchair accessible

$450

Book

Beautiful St. Michaels House Steps from Water and Town

Saint Michaels house – 20.0 mi away
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent6 Reviews

Details

Reviews

(6)

Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath, second floor has one …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(6)

Great Location, Great House, Great Time

Left on Jul 13, 2014 for a stay in July 2014

This house was perfect for a large family and very convenient for walking to sites in town. The house had a well equipped kitchen, nice backyard and barbecue grill. Within walking distance to local parks and public pool. We had nice holiday!

$350

Book

WATERFRONT SUISSE CHALET

Annapolis house
3 BR / 7 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of West Annapolis and …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great Stay, very nice location and clean home

Left on Apr 09, 2015 for a stay in April 2015

The home was located at a very continent location just 5-10mins drive to Naval academy and Annapolis downtown. The home was clean and have all the amenities. The water views from the house and easy access to the waterfront right behind the home make the stay even more memorable. I will recommend this place.

1 / 18

$200

Book

Snug Harbor USNA Cottage in Eastport Annapolis

Annapolis house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue out back on the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible
1 / 7

$450

Book

Charming Townhouse - Steps to City Dock and USNA

Annapolis house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please note - the standard …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

$250

Book

Waterfront Cottage at Spring Cove

Rock Hall cottage – 18.1 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Very Good2 Reviews

Details

Reviews

(2)

The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented to outdoor living …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Laid back and relaxing

Left on Aug 19, 2014 for a stay in August 2014

My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no expectations besides having a place to relax and hang out. We were very pleased. For a price similar to what we may have paid for one motel room elsewhere, the cottage suited our needs very well, with a fully equipped …

1 / 12

$180

Book

Captain's Quarters, a waterfront couples retreat

Rock Hall condo – 18.0 mi away
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and casual meals …
  • Pet friendly - ask
  • Suitable for children - ask
1 / 26

$595

Book

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa
5 BR / 3 BA / Sleeps 20 | Quick view

Details

Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden level, spa inspired …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
1 / 6

$295

Book

Downtown Annapolis !

Annapolis house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay Annapolis has to …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

$180

Inquire

Location Location! St Michaels-- In Town Cottage!

Saint Michaels house – 19.8 mi away
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent12 Reviews

Details

Reviews

(12)

The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(12)

Crabtastic Great Escape

Left on Aug 26, 2011 for a stay in August 2011

This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable.

I have visited this cottage several…

$350

Book

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around with a minimum of …
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask

Details

Reviews

(3)

Visitor

Left on Apr 13, 2015 for a stay in November 2014

I had the pleasure of staying at this beautiful cottage for one night. It was very clean, comfortable, and had a really cozy ambiance. The neighborhood was quiet and peaceful and it's within minutes to the downtown area by foot or car. It felt just like home! I would definitely stay here again and highly recommend it to anyone interested.

$250

Inquire

ENDLESS SUNSETS - The perfect getaway!

Claiborne house – 15.1 mi away
3 BR / 4 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake Bay. Every bedroom …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Hard to find and worth the effort

Left on Oct 10, 2014 for a stay in September 2014

Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and bathrooms galore. The only nitpick I have is the wifi seemed to fade in and out kicking us off regularly.

But with such a great view and wonderful sunsets - you won't want to be on wifi anyway.

Be sure to get good …

1 / 24

$375

Book

Charming Artists Home in Eastport/Annapolis

Annapolis house
3 BR / 4 BA / Sleeps 6 | Quick view

Details

HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous restaurants, bars, coffee …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask
1 / 23

$450

Book

Luxurious Annapolis Nautical Cottage

Annapolis cottage
2 BR / 2 BA / Sleeps 10 | Quick view

Details

Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen beds - 1 pull-out queen sleeper - 2 twins Unique Features - Walking distance to Naval Academy, downtown, shopping, restaurants and marinas - Shower for two - Off street parking for six - Completely renovated in …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 17

$250

Book

Chez Cinquai

Tilghman house – 19.8 mi away
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet kitchen, custom wood …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
1 / 15

$262

Inquire

Oak View Ridge

Maryland house – 17.1 mi away
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Bedding: Queen, Queen, 2 Twins, Double Air Mattress Delightful enchantment is what you will experience the moment that you step inside the log home Oak View Ridge. The Great Room speaks of warmth and comfort with gorgeous hardwood floors and expansive vaulted ceilings. Cuddle up in front of a crackling fireplace or …
  • Hot Tub/Jacuzzi
  • Fireplace
  • Parking
  • Grill
  • Television
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 13

$350

Inquire

10 Union Street

Annapolis house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

N/A
  • Fireplace
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Grill
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 38

$759

Book

BayCottage Waterfront Vacation Retreat St.Michaels

Saint Michaels villa – 19.2 mi away
6 BR / 6 BA / Sleeps 12 | Quick view

Details

Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are 6 bedrooms, 5.5 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask
1 / 23

$550

Inquire

Chesapeake Bay Spectacular

Stevensville house – 10.9 mi away
4 BR / 4 BA / Sleeps 14 | Quick view

Details

Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes complete with …
  • Waterfront
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 12

$450

Inquire

Chesapeake Bay Luxury Vacation Home, 5 Star

Grasonville house – 14.4 mi away
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other accommodations do not. For large…
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 8

$250

Book

Waterfront Boat Vacation Rental

Davidsonville houseboat – 11.7 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

Details

2 bedroom, 2 bath with living salon, kitchen, and an aft deck
  • Waterfront
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for the elderly - ask
1 / 17

$257

Inquire

KI Golf House:A Par for the Course&Mile from Beach

Kent Island house – 8.8 mi away
4 BR / 3 BA / Sleeps 10 | Quick view

Details

LOCATION…STAYCATION…GOLFCATION…right on Kent Island! KI Golf House: A Par for the Course Less than a mile to Dirty Dave's a gorgeous little beach and tiki bar. A short walk to the Chesapeake Bay. Call/email Donna and book it today! KI Golf House offers 4 Bedrooms, 2 ½ Baths, an open Kitchen Dining area…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 24

$595

Inquire

Winter Rates Available Quiet Relaxing Waterfront

Annapolis chalet
3 BR / 3 BA / Sleeps 10 | Quick view

Details

This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of West Annapolis and …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 24

$850

Inquire

Amazing Waterfront Annapolis & easy walk downtown

Annapolis house
4 BR / 4 BA / Sleeps 14 | Quick view

Details

A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home and property: https://youtu.be/FBqOhPJZ-qU This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible
1 / 14

$600

Book

Lavish Chesapeake Bay vacation Rental!!!!

Annapolis townhouse
1 BR / 2 BA / Sleeps 6 | Quick view

Details

This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. With access to the beach to the beach and the own …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
1 / 13

$450

Inquire

10 Minute Walk to Dwtn or Use Free Shuttle!

Annapolis house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac neighborhoods and features …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 37

$375

Inquire

Luxury vacation condominum with private beach

Chester house – 13.2 mi away
4 BR / 4 BA / Sleeps 10 | Quick view

Details

Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen size bed for the 4…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 12

$250

Inquire

Million dollar view on the Chesapeake

Deale house – 14.3 mi away
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Fredelig sted"(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you arrive. Watch the seagulls or osprey …
  • Waterfront
  • A/C or climate control
  • Porch
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 26

$262

Inquire

Sunrise Cove

Maryland house – 17.1 mi away
4 BR / 4 BA / Sleeps 11 | Quick view

Details

Bedding: King, Queen, Bunk w/trundle, Double, QSS, TSS Create unforgettable moments with family and friends when you stay in the delightful 4 bedroom lake access home Sunrise Cove. This stunning home, with its stylish décor and open floor plan, boasts the ultimate in comfort and relaxation. Fall in the love with the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Fireplace
  • A/C or climate control
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 28

$647

Inquire

Rest Assured

Maryland house – 17.1 mi away
5 BR / 5 BA / Sleeps 14 | Quick view

Details

Bedding: King, Queen, Queen, 2 Bunkbeds, 2 Bunkbeds Be “Rest Assured” that you will have a truly magical Deep Creek experience when you choose to stay in this fabulous 5 bedroom lakefront home. Evidently furnished and designed with a great deal of love and pride, you will quickly fall in love with all of the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Fireplace
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 13

$487

Inquire

Duck Cove at Wisp

Maryland house – 17.1 mi away
6 BR / 3 BA / Sleeps 16 | Quick view

Details

Community: Lake Pointe Bedding: King, Queen, Queen, Queen, Queen, 2 Twins, 2 Queen Sleeper Sofas Dove Cove at Wisp offers prime location, the most desirable amenities and the promise for an extraordinary Deep Creek vacation! Located in the prestigious community of Lake Pointe at Wisp, this home will put you in the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Fireplace
  • A/C or climate control
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 17

$321

Inquire

Breathtaking Chesapeake Bay Waterfront

Annapolis house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

2,700 Sq. Ft. Of Casual Waterfront Elegance 50' From The Chesapeake Bay ! 2,700 sq. ft. of casual waterfront elegance 50' from the shores of the Chesapeake bay and 15 minutes from historic downtown Annapolis and the Naval Academy... You will be so close to the Chesapeake Bay that your view from the kitchen looks …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 12

$980

Book

Custom-Designed Colonial Home For Your Holiday

Dundalk house – 19.1 mi away
4 BR / 3 BA / Sleeps 10 | Quick view

Details

You will really comfortable by chosing this nearly-new, custom-designed colonial that has a distinct contemporary flair - decorated in gorgeous, neutral d~cor!!2 acres of land - soaring ceilings, gleaming wood floors - and a family room/kitchen design that everyone wants: gourmet kitchen w/convenient granite bar for …
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Linens Provided
    1 / 12

    $650

    Book

    Lavish and Upscale Vacation Rental

    Annapolis apartment
    1 BR / 3 BA / Sleeps 6 | Quick view

    Details

    This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. The security guard at the booth adds a feeling of …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • A/C or climate control
    • Balcony or terrace

      $350

      Book

      *BOOK NOW* Beautiful Cottage in historic Annapolis

      Annapolis cottage
      3 BR / 2 BA / Sleeps 6 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around with a minimum of …
      • Internet Access
      • Fireplace
      • Outdoor Dining Area
      • A/C or climate control
      • Central heating
      • Suitable for children - ask

      Details

      Reviews

      (3)

      Charming cottage walking distance to downtown Annapolis.

      Left on Mar 26, 2015 for a stay in March 2015

      My husband and I had a wonderful stay at this quiet cottage home. It is walking distance to downtown Annapolis. It was very clean and comfortable, we had a great night sleep on such a comfortable bed. The little side porch is so cute for morning coffee! The owners were right next door in case we had any questions and they were very helpful in pointing out restaurants and sights in the area. …

      1 2
      page 1 of 2
      Load more