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Boston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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.
The price is ￥13,936
￥47,526 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥16,137
￥58,335 total
includes taxes & fees
Oct 25 - Oct 26
Sprawling Updated Ranch with Fireplace on Wimbledon
A living room with a fireplace, large windows, and a chandelier.

3. The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (37 reviews)
"Wonderful property with the absolute best location!"
United States
Scott A.
The price is ￥14,670
￥42,330 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥14,670
￥56,435 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥15,516
￥51,069 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥14,670
￥52,799 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥16,151
￥57,132 total
includes taxes & fees
Oct 26 - Oct 27
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.
The price is ￥14,670
￥55,182 total
includes taxes & fees
Nov 2 - Nov 3
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)
"Great place, perfect for the weekend. "
United States
bill W.
The price is ￥14,670
￥53,740 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is ￥12,469
￥49,044 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is ￥26,487
￥55,175 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥23,510
￥28,996 total
includes taxes & fees
Oct 26 - Oct 27
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.
The price is ￥16,137
￥57,395 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥23,493
￥66,786 total
includes taxes & fees
Nov 1 - Nov 2
Southern Charm Home: Pool + Fireplace + Large Yard
Living area

15. Bobwhite Bungalow - Thomasville, GA

Bobwhite Bungalow - Thomasville, GA
Thomasville
The price is ￥25,390
￥33,527 total
includes taxes & fees
Oct 25 - Oct 26
Bobwhite Bungalow - Thomasville, GA
A wooden deck with wicker chairs and a glass table.

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, (9 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.
The price is ￥19,591
￥51,250 total
includes taxes & fees
Nov 8 - Nov 9
New!! Remodeled downtown home. Golf cart available to rent. Walk to Broad St.
Room

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)
The price is ￥24,707
￥42,590 total
includes taxes & fees
Oct 27 - Oct 28
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.
The price is ￥13,067
￥48,027 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is ￥17,326
￥59,813 total
includes taxes & fees
Nov 4 - Nov 5
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
The price is ￥13,836
￥32,475 total
includes taxes & fees
Oct 25 - Oct 26
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

Home Sweet Home

Home Sweet Home

10/10 Excellent
"We had a wonderful stay and the check in process was very smooth! We would definitely stay here again!"
Bryan P. 2-night trip
Posted 1 day ago
Home Sweet Home

Find out more about Boston

Search for holiday rentals in Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in Boston using one of the methods below:

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Look no further and take a look at our great range of rental properties in Boston!

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.