Vacation rentals in Talbot County

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Top-rated vacation rentals in Talbot County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 418 reviews

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

Mar 21 – 28

€ 218 per night
Guest favorite

Apartment in Stevensville

4.97 out of 5 average rating, 239 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Aug 17 – 24

€ 203 per night
Guest favorite

Guest suite in Cambridge

4.95 out of 5 average rating, 265 reviews

Oakley Suite

5 minute walk to restaurants and shops, 3 min.to the water. Ideal setting with lovely rear patio and garden with entrance to private family room. Stairs to upper level with 2 very large and private guest rooms. Landing at top of steps presents a convenience station with Keurig, microwave, and mini fridge. This Suite is completely private and includes 2 bedrooms, bath, family room, convenience station, and rear patio, all for one price! 1st floor Owners Suite available as well for a total of 8 !

Aug 23 – 30

€ 139 per night

Popular amenities for Talbot County vacation rentals

Other great vacation rentals in Talbot County

Guest favorite

Condo in Oxford

4.98 out of 5 average rating, 112 reviews

Cozy Oxford Getaway

Apr 6 – 13

€ 186 per night
Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

Nov 10 – 17

€ 90 per night
Guest favorite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

Jul 26 – Aug 2

€ 136 per night
Guest favorite

Guesthouse in Wye Mills

4.93 out of 5 average rating, 15 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

Sep 23 – 30

€ 99 per night
Superhost

Home in Bozman

5.0 out of 5 average rating, 5 reviews

Grace Creek Cottage

May 22 – 29

€ 413 per night
Guest favorite

Cottage in Easton

5.0 out of 5 average rating, 83 reviews

Cottage on Solitude Creek, Hot Tub & Firepit

Apr 17 – 24

€ 394 per night
Guest favorite

Home in Easton

5.0 out of 5 average rating, 17 reviews

Eastern Shore Retreat!

Dec 14 – 21

€ 469 per night
Guest favorite

Home in Easton

5.0 out of 5 average rating, 40 reviews

Tuckaway Cove Relaxing waterfront property

Oct 30 – Nov 6

€ 798 per night
Guest favorite

Home in Oxford

5.0 out of 5 average rating, 37 reviews

Stunning Chesapeake waterfront home

Dec 16 – 23

€ 721 per night
Guest favorite

Barn in Queenstown

5.0 out of 5 average rating, 40 reviews

Waterfront Modern Guest Barn

Aug 23 – 30

€ 633 per night
Guest favorite

Home in Saint Michaels

4.98 out of 5 average rating, 81 reviews

SM’s Premier Rental Heated Pool opens 4/12

Mar 6 – 13

€ 783 per night
Guest favorite

Home in Newcomb

5.0 out of 5 average rating, 28 reviews

Saint Michaels Waterfront Home

Nov 6 – 13

€ 605 per night

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