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Talbot County Rentals

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48 Houses

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,115

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

Price per night from

$515

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$351

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 3 minutes

Price per night from

$857

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$217

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$296

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$430

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$205

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$381

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$320

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$217

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Price per night from

$6,859

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$782

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 9

“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite. As for the house itself, we couldn't have asked for more. It is spacious, clean, and has all of the amenities you could want. I must also mention that it was a breeze and a pleasure working with the folks at Grandview. They are incredibly responsive, and make a great effort to ensure that you enjoy your stay.

Price per night from

$547

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$440

Ship's Cove Inn and Resort

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,284

Great rentals within 20 miles that match your search

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$794

Vintage Bungalow-cozy, walkable, free pkg.

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$486

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$514

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Price per night from

$400

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” 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 first contacted him about renting.

Price per night from

$451

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$914

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,142

Tentrr Signature Site - Wye Island View

Grasonville tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$258

Responds fast! avg. 1 hour 4 minutes

Price per night from

$458

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$486

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$183

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$229

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$799

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$189

22 Fleet St. - Best Spot for Commissioning Week, Newly-Renovated & Historic!

Annapolis condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$302

Luxury Home Walkable to Main Street w Parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$194

Historic Charm! Walk to Annapolis Waterfront & Academy

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Price per night from

$471

Newly-renovated home in waterfront community available now!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 16 minutes

Price per night from

$381

Newly Managed Randall House in Downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 16 minutes

Price per night from

$410

Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$287

Newly Managed Guest Suite in Eastport

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 16 minutes

Price per night from

$251

Lux Downtown Annapolis Home with 3 parking spots!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Price per night from

$381

Viewing 38 of 48
rentals in Talbot County

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Top Destination reviews

Sandy Pines: Enjoy Harris Creek w/Pool and Boats
Family friendly

We went to the wine feast in Saint Michael's had a great time. Stay with Mom, 87 years old and four sisters. We went boat riding and enjoying the porch play games and cards. … see more
Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
Perfect cottage for a relaxing stay in St. Michaels!

My husband and two kids (toddler and infant) visited the Carpenter St. cottage in St. Michaels as our first family vacation getaway since our youngest was born. This beautiful rental was absolutely the perfect fit for us! The location is unbeatable - in one direction, it's steps to the water, in the other, it's steps to Talbot St. restaurants, shops, etc. The owners have done a lovely job decorating the cottage, and we found it exceptionally functional for our stay. We loved the updated kitchen, which opens to a family room/dining room combo, and ADORED the huge screened in patio that looks out over the beautiful yard (which my toddler loved playing in). We probably spent half our time on the patio! Additionally, we loved the enormous master suite on the second floor of the home - in addition to the comfortable king sized bed, there was plenty of room for our pack n play and infant bed. If you're looking for a nice home to relax in, close to everything, you can't beat this home! The owners were great and very easy to deal with. We have already booked our next vacation here!see more
Location Location! St Michaels-- In Town Cottage!
Stepping back in history with today's amenities

This cottage was very nicely restored to capture the historic feel of colonial times, yet equipped with the modern conveniences. Since we visited during the winter, we especially enjoyed the fireplace. The location was convenient--within walking distance to shops and restaurants. It was tough to leave such a relaxing and comfortable cottage, we will definitely be back!see more
Cottage 2 at Grandview Pleasure Point
Wonderful!

Our family has been vacationing at Grandview for over 20 years. I think that says it all. Beautiful location, gorgeous sunsets, peaceful and quite. Serene. Plenty of crabbing, swimming, fishing and just plan relaxing. The cottages are nicely furnished, cozy, clean and well-stocked kitchen. Plenty to do in the area-close to St. Michaels, hiking, cycling, nice restaurants. We love it here.see more
Large Historic Thomas Harrison House on Harbor in St. Michaels Town
Comfortable, large home with perfect location!

My daughter was married in St. Michaels in May so I rented this house and filled it with family. It was a perfect "home base" for all of the activities surrounding the wedding, walking distance to all of the shops, restaurants, hotels and activities on the harbor. Although parking is limited on the narrow streets, there's a large town lot just a few steps from the house and we were always able to unload or drop the senior citizens off right at the front door. My granddaughters loved the fenced yard which is right off the kitchen and we adults enjoyed watching them play from the rockers on the covered porch. My only problem is that I was so busy that I didn't have enough time to just relax and enjoy the amazing water views or explore the area. I intend to go back to this house with the same group and more leisure time!see more
Premier Cottage in St. Michaels- In Town Location!
This house has it all.....

I stayed at the Blades house last week and everything was just what we wanted. The location is beyond perfect (in walking distance of everything) and the house had all of the amenities we were looking for. Very spacious, cozy, with a screened in back porch that was perfect for relaxing outside during the evening. Spacious kitchen and living room perfect for a nice relaxing weekend getaway. We will definitely be staying here again for sure!see more

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