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Boston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Boston vacation rentals

A kitchen with grey cabinets, a stainless steel refrigerator, a black countertop, and a window with a view of the backyard.

1. Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (65 reviews)
"This property was in a wonderful location"
United States
Cornelia D.
$295 nightly
The price is $315
Nov 2 - Nov 3
Total with taxes and fees
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
A spacious living room with a fireplace, green armchairs, a white sofa, and a ceiling fan.

2. Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.8 out of 10, Exceptional, (23 reviews)
"The Place was very comfortable and clean. "
United States
David Y.
$348 nightly
The price is $372
Oct 28 - Oct 29
Total with taxes and fees
Sprawling Updated Ranch with Fireplace on Wimbledon
A storefront with a sign for a farm shop and grocery, a potted plant, and a bench on the sidewalk.

3. The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (37 reviews)
"Awesome location downtown. Great views!"
United States
James H.
$253 nightly
The price is $270
Oct 28 - Oct 29
Total with taxes and fees
The Roost - Downtown Thomasville
A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a central island with bar stools.

4. Modern Home Near Downtown Thomasville

Modern Home Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (33 reviews)
"Convenient location. Comfortable house to come home to after a long day looking around Thomasville and the area."
United States
Myra K.
$337 nightly
The price is $360
Oct 28 - Oct 29
Total with taxes and fees
Modern Home Near Downtown Thomasville
A red door with a glass panel, a welcome sign, a blue chair, and steps leading to the entrance.

5. Whispering Pines Court in Historical Thomasville

Whispering Pines Court in Historical Thomasville
Thomasville
10.0 out of 10, Exceptional, (1 review)
"Sheryl’s home was perfect for my husband’s business trip. It was comfortable, well-kept, and in a great location. I would definitely recommend it to anyone visiting the Thomasville area."
United States
Micca J.
$294 nightly
The price is $341
Oct 28 - Oct 29
Total with taxes and fees
Whispering Pines Court in Historical Thomasville
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

6. Mimosa Stay Cottage - Thomasville Close to all the Charm

Mimosa Stay Cottage - Thomasville Close to all the Charm
Thomasville
10.0 out of 10, Exceptional, (8 reviews)
"Very well appointed accommodations in a quiet neighborhood. It was perfect for our needs and near the hospital."
United States
Sheri B.
$318 nightly
The price is $340
Oct 28 - Oct 29
Total with taxes and fees
Mimosa Stay Cottage - Thomasville Close to all the Charm
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

7. Newly Built, Stunning 4BR/2BA with Waterfront Views

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
10.0 out of 10, Exceptional, (26 reviews)
"Very clean! Perfect home for hosting my guests that were in town visiting!"
United States
Kristen M.
$348 nightly
The price is $372
Oct 28 - Oct 29
Total with taxes and fees
Newly Built, Stunning 4BR/2BA with Waterfront Views
A deck with a table and chairs overlooking a lake, surrounded by trees and a grassy area.

8. Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Thomasville
9.2 out of 10, Wonderful, (11 reviews)
"This was not our first time to T’ville so knew the location and experience we would have in the town. We chose the vrbo based on proximity and availability. "
United States
Lori W.
$340 nightly
The price is $363
Nov 1 - Nov 2
Total with taxes and fees
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

9. Mimosa Getaway - Less than 1 mile from Downtown

Mimosa Getaway - Less than 1 mile from Downtown
Thomasville
9.6 out of 10, Exceptional, (15 reviews)
"Fantastic place! Fully renovated. Perfect for our family needs. The bunk beds were ideal. Would stay again next time we’re in Thomasville!"
United States
Nathan W.
$323 nightly
The price is $345
Oct 28 - Oct 29
Total with taxes and fees
Mimosa Getaway - Less than 1 mile from Downtown
A spacious living room with a fireplace, a dining area, and a bedroom with a large window.

10. Mimosa Cottage - Near Downtown Thomasville

Mimosa Cottage - Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (25 reviews)
"Stay and area was Great!"
United States
Geoff
$290 nightly
The price is $310
Nov 1 - Nov 2
Total with taxes and fees
Mimosa Cottage - Near Downtown Thomasville
A porch with a ceiling fan, a green door, and a potted plant.

11. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (148 reviews)
"It was a great house and location. Beds were comfortable. Location was great. Well stocked."
United States
Nita P.
$304 nightly
The price is $352
Oct 28 - Oct 29
Total with taxes and fees
QUAIL COTTAGE - Downtown Thomasville!
A hallway with a wooden barn-style door, a kitchen area with a sink and cabinets, and a framed picture on the wall.

12. Dog friendly nature preserve Monticello, FL

Dog friendly nature preserve Monticello, FL
Monticello
10.0 out of 10, Exceptional, (3 reviews)
"Nice rustic environment and very pet friendly."
United States
Jeff B.
$171 nightly
The price is $186
Oct 28 - Oct 29
Total with taxes and fees
Dog friendly nature preserve Monticello, FL
A compact kitchen with a refrigerator, a trash bin, and a door with a curtain.

13. The Walcott Cottage: Walkable Historic Retreat in Thomasville

The Walcott Cottage: Walkable Historic Retreat in Thomasville
Dawson Street Historic District
10.0 out of 10, Exceptional, (1 review)
"This place was perfect. It had everything I needed. Location was perfect also."
United States
dorothy k.
$342 nightly
The price is $366
Oct 28 - Oct 29
Total with taxes and fees
The Walcott Cottage: Walkable Historic Retreat in Thomasville
A kitchen with a marble island, white cabinetry, and a hanging light fixture.

14. Southern Charm Home: Pool + Fireplace + Large Yard

Southern Charm Home: Pool + Fireplace + Large Yard
Thomasville
10.0 out of 10, Exceptional, (9 reviews)
"Nice location - convenient to town and very quiet! House and pool area were clean and comfortable."
United States
Trey H.
$398 nightly
The price is $426
Nov 1 - Nov 2
Total with taxes and fees
Southern Charm Home: Pool + Fireplace + Large Yard
Living area

15. Bobwhite Bungalow - Thomasville, GA

Bobwhite Bungalow - Thomasville, GA
Thomasville
$183 nightly
The price is $214
Oct 28 - Oct 29
Total with taxes and fees
Bobwhite Bungalow - Thomasville, GA
A kitchen with wooden cabinets, a microwave, an oven, a dishwasher, and granite countertops.

16. New!! Remodeled downtown home. Golf cart available to rent. Walk to Broad St.

New!! Remodeled downtown home. Golf cart available to rent. Walk to Broad St.
Thomasville
10.0 out of 10, Exceptional, (10 reviews)
"Our favorite VRBO served stayed in! Clean, cozy, great location to downtown Thomasville. We loved our stay. And our hosts we super helpful and friendly! 10 star stay"
United States
Cody D.
$271 nightly
The price is $314
Nov 8 - Nov 9
Total with taxes and fees
New!! Remodeled downtown home. Golf cart available to rent. Walk to Broad St.
A two-story house with a front porch, a brick staircase, and a well-maintained lawn.

17. The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11

The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11
Thomasville
10.0 out of 10, Exceptional, (5 reviews)
$233 nightly
The price is $272
Nov 5 - Nov 6
Total with taxes and fees
The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11
A wooden deck with a table set for two, surrounded by chairs, overlooking a forested area.

18. An elegant waterside retreat in the Red Hills

An elegant waterside retreat in the Red Hills
Thomasville
9.6 out of 10, Exceptional, (34 reviews)
"Great stay very peaceful "
United States
Chrisy O.
$288 nightly
The price is $308
Nov 2 - Nov 3
Total with taxes and fees
An elegant waterside retreat in the Red Hills
A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining table with chairs.

19. Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Thomasville
9.4 out of 10, Exceptional, (35 reviews)
"We loved the location and enjoyed the back yard."
United States
Grace F.
$348 nightly
The price is $372
Oct 28 - Oct 29
Total with taxes and fees
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
A house with a covered patio area, a staircase, and a car parked in the driveway.

20. Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible

Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible
Monticello
9.8 out of 10, Exceptional, (24 reviews)
"Our stay was perfect! The cottage was clean, it had all everything needed to be comfortable. The area was super quiet which allowed for a great rest. I would totally recomend !"
United States
Richard
$188 nightly
The price is $205
Nov 1 - Nov 2
Total with taxes and fees
Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible
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 Boston Hotel Reviews

Holiday Inn Express & Suites Thomasville by IHG

Holiday Inn Express & Suites Thomasville by IHG

10/10 Excellent
"i was there for a family gathering the room was clean and staff was very friendly. i will definitely be back and i will recommend to friends and family. Thanks"
Glenda 2-night trip
Posted 9 hours ago
Holiday Inn Express & Suites Thomasville by IHG

Find out more about Boston

Everything you need to know about Boston 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 Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Boston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Boston vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $214 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston 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 Boston 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 Boston 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 Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Boston?

Yes, you can find vacation rentals near well known attractions in Boston, or you can go with a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Boston?

Sprawling Updated Ranch with Fireplace on Wimbledon: This vacation home rental near Boston is located in the city center and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Boston?

While exploring the area, visit the sights like Thomasville's Historic Big Oak, Lapham-Patterson House, and Pebble Hill Plantation. In the larger area, you’ll find Sweet Grass Dairy Marketplace and Jack Hadley Black History Museum.

What’s a vacation rental in Boston like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Boston. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip.