Talbot County Rentals

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64 Houses

Waterfront Room Rentals 2 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 46 minutes

Price per night from

$115

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

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,117

Waterfront Room Rentals 1 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 46 minutes

Price per night from

$150

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

Price per night from

$378

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$572

Waterfront Room Rentals 3 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 46 minutes

Price per night from

$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.

Responds fast! avg. 3 hours 23 minutes

Price per night from

$447

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$216

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” 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 times and will continue to do so! A great place to gather with family and friends or a quick weekend escape to enjoy life on the shore.

Responds fast! avg. 3 hours 23 minutes

Price per night from

$224

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

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 23 minutes

Price per night from

$247

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$212

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$338

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

$263

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$687

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 37 minutes

Price per night from

$859

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$258

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 23 minutes

Price per night from

$235

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 23 minutes

Price per night from

$247

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$785

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$216

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 45 minutes

Price per night from

$160

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$373

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“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

$651

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$441

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 35 minutes

Price per night from

$1,146

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$413

Great rentals within 20 miles that match your search

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 56 minutes

Price per night from

$368

Your Eastport Annapolis Haven!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 16 minutes

Price per night from

$484

Summer House in Rock Hall

Rock Hall house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 1 hour 56 minutes

Price per night from

$327

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$459

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 56 minutes

Price per night from

$432

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 43 minutes

Price per night from

$86

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

$327

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 45 minutes

Price per night from

$134

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 56 minutes

Price per night from

$313

Maryland’s Eastern Shore Welcomes You

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 43 minutes

Price per night from

$100

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,146

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,603

Viewing 38 of 64
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
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
Waterfront Room Rentals 2 with Private Beach
Amazing location and view of water

Huge home with many rooms. Owner very nice. It is up for sale however. Easy access to Cambridge if you're doing the triathlon. … see more
Pot Pie House
Lovely

We had a wonderful time in Pot Pie. Neighbors are very nce. We felt that we are in our home. Place was well kept. Will definitely go back & maybe spend some time with Elaine & Joe. Highly recommended... … see more

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