Default HTG hotel image

Boston Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Boston vacation rentals

A hallway with a wooden barn-style door, a kitchen area with a sink and cabinets, and a framed picture on the wall.

1. 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.
$198 nightly
The price is $216
Sep 9 - Sep 10
Total with taxes and fees
Dog friendly nature preserve Monticello, FL

2. The Budd-Pafford House: The Rose Room

The Budd-Pafford House: The Rose Room
Monticello
8.2 out of 10, Very Good, (10 reviews)
"Easy location to access. Friendly host."
United States
Mary Ellen W.
$200 nightly
The price is $218
Sep 9 - Sep 10
Total with taxes and fees
The Budd-Pafford House: The Rose Room

3. The Budd-Pafford House - The Exploration Suite

The Budd-Pafford House - The Exploration Suite
Monticello
9.0 out of 10, Wonderful, (13 reviews)
"Beautiful place with large rooms and great communication. The house was amazing and the town adorable."
United States
Angela M.
$226 nightly
The price is $246
Sep 9 - Sep 10
Total with taxes and fees
The Budd-Pafford House - The Exploration Suite
A house with a covered patio area, a staircase, and a car parked in the driveway.

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

Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible
Monticello
9.6 out of 10, Exceptional, (20 reviews)
"Cute house in great location. "
United States
Dan L.
$188 nightly
The price is $205
Sep 20 - Sep 21
Total with taxes and fees
Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible
A modern kitchen with a white island, wooden bar stools, and a large window with blinds.

5. Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
Monticello
10.0 out of 10, Exceptional, (24 reviews)
"Such a cute property. Clean and well maintained"
United States
Martha H.
$298 nightly
The price is $325
Sep 9 - Sep 10
Total with taxes and fees
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
A deck with a table and chairs overlooking a lake, surrounded by trees and a grassy area.

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

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Thomasville
9.6 out of 10, Exceptional, (10 reviews)
"Great place"
United States
Michael S.
$336 nightly
The price is $359
Sep 13 - Sep 14
Total with taxes and fees
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
A kitchen with a marble island, white cabinetry, and a hanging light fixture.

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

Southern Charm Home: Pool + Fireplace + Large Yard
Thomasville
10.0 out of 10, Exceptional, (8 reviews)
"Convenient location and has everything you need."
United States
Dee J.
$427 nightly
The price is $457
Sep 29 - Sep 30
Total with taxes and fees
Southern Charm Home: Pool + Fireplace + Large Yard
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
10.0 out of 10, Exceptional, (22 reviews)
"The property was clean and spacious for our family. The access were very easy."
United States
Frederick E
$351 nightly
The price is $375
Sep 9 - Sep 10
Total with taxes and fees
Newly Built, Stunning 4BR/2BA with Waterfront Views
A spacious living room with a fireplace, green armchairs, a white sofa, and a ceiling fan.

9. Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.8 out of 10, Exceptional, (21 reviews)
"The Place was very comfortable and clean. "
United States
David Y.
$347 nightly
The price is $371
Sep 13 - Sep 14
Total with taxes and fees
Sprawling Updated Ranch with Fireplace on Wimbledon
A red door with a glass panel, a welcome sign, a blue chair, and steps leading to the entrance.

10. 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.
$219 nightly
The price is $256
Oct 5 - Oct 6
Total with taxes and fees
Whispering Pines Court in Historical Thomasville
A log cabin with a large porch, multiple windows, and a wooden roof.

11. Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
Thomasville
10.0 out of 10, Exceptional, (13 reviews)
"Amazing property. We stayed here as a family vacation just to get away and it was a treat to enjoy such an awesome home."
United States
Matt P.
$616 nightly
The price is $660
Sep 9 - Sep 10
Total with taxes and fees
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
A living room with a red leather sofa, a white sofa, a wooden coffee table, and a patterned rug.

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

The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11
Thomasville
$228 nightly
The price is $266
Sep 14 - Sep 15
Total with taxes and fees
The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11
A two-story house with a front porch, a staircase leading to the entrance, and a garden with various plants.

13. Treehouse views in Historic Downtown Thomasville, Georgia

Treehouse views in Historic Downtown Thomasville, Georgia
Thomasville
10.0 out of 10, Exceptional, (11 reviews)
"Great location, very comfortable and charming home."
United States
Betsy H.
$360 nightly
The price is $415
Sep 9 - Sep 10
Total with taxes and fees
Treehouse views in Historic Downtown Thomasville, Georgia
A kitchen with grey cabinets, a stainless steel refrigerator, a black countertop, and a window with a view of the backyard.

14. Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (63 reviews)
"Enjoyed our stay very much."
United States
Barbara F.
$279 nightly
The price is $299
Sep 13 - Sep 14
Total with taxes and fees
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

15. Mimosa Getaway - Less than 1 mile from Downtown

Mimosa Getaway - Less than 1 mile from Downtown
Thomasville
9.6 out of 10, Exceptional, (14 reviews)
"Great place, perfect for the weekend. "
United States
bill W.
$320 nightly
The price is $342
Sep 13 - Sep 14
Total with taxes and fees
Mimosa Getaway - Less than 1 mile from Downtown
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

16. 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, (6 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
Sep 20 - Sep 21
Total with taxes and fees
Mimosa Stay Cottage - Thomasville Close to all the Charm
A spacious living room with a fireplace, a dining area, and a bedroom with a large window.

17. Mimosa Cottage - Near Downtown Thomasville

Mimosa Cottage - Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (22 reviews)
"Stay and area was Great!"
United States
Geoff
$295 nightly
The price is $315
Sep 28 - Sep 29
Total with taxes and fees
Mimosa Cottage - Near Downtown Thomasville
A dining area with a wooden table and chairs, a chandelier, and large windows with blue shutters.

18. The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Thomasville
10.0 out of 10, Exceptional, (23 reviews)
"Our stay was absolutely wonderful! Will definitely be booking here again!"
United States
Unspecified U.
$335 nightly
The price is $387
Sep 9 - Sep 10
Total with taxes and fees
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
A porch with a ceiling fan, a green door, and a potted plant.

19. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (143 reviews)
"Very nice home. Communication was excellent! We would stay here again."
United States
colleen z.
$306 nightly
The price is $354
Sep 9 - Sep 10
Total with taxes and fees
QUAIL COTTAGE - Downtown Thomasville!
A wooden deck with a table set for two, surrounded by chairs, overlooking a forested area.

20. An elegant waterside retreat in the Red Hills

An elegant waterside retreat in the Red Hills
Thomasville
9.6 out of 10, Exceptional, (33 reviews)
"Great stay very peaceful "
United States
Chrisy O.
$288 nightly
The price is $308
Sep 9 - Sep 10
Total with taxes and fees
An elegant waterside retreat in the Red Hills
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Boston Hotel Reviews

Home2 Suites By Hilton Thomasville

Home2 Suites By Hilton Thomasville

10/10 Excellent
"Everything about this hotel was good. I really love the breakfast and the room was nicely put together."
Christie 1-night trip
Posted 9 hours ago
Home2 Suites By Hilton Thomasville

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 $216 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?

QUAIL COTTAGE - Downtown Thomasville!: This vacation home near Boston is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Thomasville Genealogical, History and Fine Arts Library.

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.