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Talbot County Vacation Rentals

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Top cities in Talbot County

A lighthouse on stilts with a green roof, surrounded by water and greenery.
Vacation Rentals

St. Michaels

St. Michaels

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Talbot County vacation rentals

Living area

1. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is CA $357
CA $588 total
includes taxes & fees
Nov 30 - Dec 1
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A living room with two grey sofas, a coffee table, and a ceiling fan.

2. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is CA $136
CA $461 total
includes taxes & fees
Nov 16 - Nov 17
Cambridge Apt in Walkable Neighborhood
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

3. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is CA $243
CA $526 total
includes taxes & fees
Dec 15 - Dec 16
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

4. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $221
CA $345 total
includes taxes & fees
Nov 16 - Nov 17
Sailwinds Loft at Cambridge Creek
A marina with boats docked, a water tower, and residential buildings with balconies.

5. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is CA $300
CA $810 total
includes taxes & fees
Nov 16 - Nov 17
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

6. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is CA $146
CA $438 total
includes taxes & fees
Nov 23 - Nov 24
Relax on Kent Island in 4 Bedroom Home w/Waterview
A waterfront patio with outdoor seating and umbrellas, overlooking a river with boats and a bridge in the background.

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (113 reviews)
"Great hosts!! Great property and location!!"
United States
Lora W.
Cass-Away Luxury Houseboat
An outdoor seating area with tables and chairs, umbrellas, and a view of the water.

8. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
The price is CA $997
CA $1,797 total
includes taxes & fees
Dec 1 - Dec 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

9. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is CA $571
CA $897 total
includes taxes & fees
Dec 7 - Dec 8
Turnbridge Manor
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

10. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is CA $243
CA $525 total
includes taxes & fees
Dec 15 - Dec 16
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A deck with a view of a marina, including boats and docks.

11. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
Cass-N-Reel Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

12. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (51 reviews)
"Great stay"
United States
Michael V.
The price is CA $146
CA $438 total
includes taxes & fees
Nov 23 - Nov 24
Charming Coastal/Country Home w/3 Acres & Sauna!
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

13. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $385
CA $443 total
includes taxes & fees
Nov 24 - Nov 25
Family Friendly Cozy 3 Bedroom Duplex
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

14. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $363
CA $663 total
includes taxes & fees
Nov 19 - Nov 20
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A living room with two grey sofas, a coffee table, and a ceiling fan.

15. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveller
The price is CA $94
CA $450 total
includes taxes & fees
Nov 16 - Nov 17
Cambridge Apt in Walkable Neighborhood
A dining area with a round table, chairs, and a decorative table runner.

16. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is CA $425
CA $556 total
includes taxes & fees
Nov 16 - Nov 17
More, than just a place to sleep - welcome home!
A two-story house with a porch, two windows, and a door.

17. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
The price is CA $321
CA $501 total
includes taxes & fees
Dec 1 - Dec 2
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

18. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $997
CA $1,797 total
includes taxes & fees
Dec 1 - Dec 2
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

19. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is CA $321
CA $371 total
includes taxes & fees
Nov 16 - Nov 17
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

20. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is CA $350
CA $402 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront Getaway with Dock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Talbot County Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

Find out more about Talbot County

Everything you need to know about Talbot County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Talbot County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Talbot County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Talbot County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Talbot County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Talbot County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Talbot County vacation rentals we have selected for you start as low as CA $135 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Talbot County rentals

At Expedia, we put the best Talbot County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Talbot County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Talbot County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Talbot County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.