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Talbot County Rentals

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69 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.

Responds fast! avg. 3 hours 6 minutes

Price per night from

$515

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 6 minutes

Price per night from

$351

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 4 minutes

Price per night from

$857

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$218

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 6 minutes

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

Responds fast! avg. 3 hours 6 minutes

Price per night from

$430

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 6 minutes

Price per night from

$382

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

$218

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$6,856

Main House at Grandview at Pleasure Point

Bozman house

4 bedrooms / 3 bathrooms / sleeps 9

“Family Fun at Grandview” Our group of grandparents, children with spouses, & grandchildren spent a week in the main house at Grandview. We had a great time in the pool, on the docks, in the porches, & exploring this very large & private property. We also enjoyed the shopping, restaurants, & Maritime Museum in St. Michaels. It was a very hot week & the many fans that were provided made it comfortable. The kitchen was well equipped to handle a large group & we had a great seafood feast on the picnic tables by the pool.

Price per night from

$663

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

$715

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$2,286

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

8 bedrooms / 10 bathrooms / sleeps 12

Price per night from

$2,857

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,286

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$1,886

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Neavitt manor house

25 bedrooms / 25 bathrooms / sleeps 50

Price per night from

$8,570

Great rentals within 20 miles that match your search

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

$452

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$1,023

Golf..Fish..Hunt..Shop - A PAR for the Course & Mile to Beach on Kent Island

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$772

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

$457

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$800

Responds fast! avg. 55 minutes

Price per night from

$457

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$1,943

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,943

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,143

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$399

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

5 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$160

Tentrr Signature Site - Wye Island View

Grasonville tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 44 minutes

Price per night from

$229

Breathtaking Waterfront Cambridge Getaway

Cambridge house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$680

Charming 3 bdrm cottage with lovely front porch

Rock Hall house

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$228

Cozy Downtown Annapolis Apartment

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$247

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$183

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$189

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$343

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$799

Brazilian Artsy Townhome- The wooded getaway

Cape Saint Claire house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$286

Viewing 38 of 69
rentals in Talbot County

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Top Destination reviews

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
Main House at Grandview at Pleasure Point
Great place for our business retreat

This house was the perfect size for our staff of 8 for our annual staff retreat. The rooms were comfortable. The size of the dining room table was great for our meetings. We enjoyed quiet time sitting on the dock by the water and on the deck. We also learned the art of crabbing as well. We would definitely rent again for future staff retreats.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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