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Boston Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Boston vacation rentals

TV, books

1. Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.8 out of 10, Exceptional, (22 reviews)
"The Place was very comfortable and clean. "
United States
David Y.
The price is AED 378
AED 1,297 total
includes taxes & fees
29 Sep - 30 Sep
Sprawling Updated Ranch with Fireplace on Wimbledon
Outdoor dining

2. 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.
The price is AED 413
AED 1,334 total
includes taxes & fees
27 Oct - 28 Oct
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Outdoor dining

3. 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.
The price is AED 306
AED 1,077 total
includes taxes & fees
29 Sep - 30 Sep
An elegant waterside retreat in the Red Hills
2 bedrooms, iron/ironing board, WiFi, bed sheets

4. 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 AED 354
AED 1,168 total
includes taxes & fees
28 Oct - 29 Oct
Mimosa Cottage - Near Downtown Thomasville
Coffee/tea maker, fridge, microwave, oven

5. 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 AED 344
AED 1,197 total
includes taxes & fees
29 Sep - 30 Sep
Mimosa Getaway - Less than 1 mile from Downtown
Interior

6. 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 AED 643
AED 781 total
includes taxes & fees
29 Sep - 30 Sep
Dog friendly nature preserve Monticello, FL
TV, books

7. 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, (7 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 AED 344
AED 1,179 total
includes taxes & fees
29 Sep - 30 Sep
Mimosa Stay Cottage - Thomasville Close to all the Charm
Coffee/tea maker, fridge, microwave, oven

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

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
10.0 out of 10, Exceptional, (23 reviews)
"The property was clean and spacious for our family. The access were very easy."
United States
Frederick E
The price is AED 378
AED 1,297 total
includes taxes & fees
4 Oct - 5 Oct
Newly Built, Stunning 4BR/2BA with Waterfront Views
TV, books

9. 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 AED 344
AED 959 total
includes taxes & fees
29 Sep - 30 Sep
The Roost - Downtown Thomasville
Coffee/tea maker, fridge, microwave, oven

10. Modern Home Near Downtown Thomasville

Modern Home Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (32 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 AED 378
AED 1,294 total
includes taxes & fees
27 Oct - 28 Oct
Modern Home Near Downtown Thomasville
Interior

11. 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 AED 378
AED 1,279 total
includes taxes & fees
29 Sep - 30 Sep
The Walcott Cottage: Walkable Historic Retreat in Thomasville
Exterior detail

12. 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 AED 364
AED 1,153 total
includes taxes & fees
5 Oct - 6 Oct
Whispering Pines Court in Historical Thomasville
Coffee/tea maker, fridge, microwave, oven

13. Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (64 reviews)
"This property was in a wonderful location"
United States
Cornelia D.
The price is AED 399
AED 1,177 total
includes taxes & fees
14 Oct - 15 Oct
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Coffee/tea maker, fridge, microwave, oven

14. 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, (34 reviews)
"We loved the location and enjoyed the back yard."
United States
Grace F.
The price is AED 378
AED 1,297 total
includes taxes & fees
29 Sep - 30 Sep
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Exterior detail

15. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (146 reviews)
"This was my 2nd stay at Quail Cottage. Highly recommend! "
United States
Misti B.
The price is AED 621
AED 1,238 total
includes taxes & fees
29 Sep - 30 Sep
QUAIL COTTAGE - Downtown Thomasville!
Terrace/patio

16. 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, (22 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 AED 360
AED 793 total
includes taxes & fees
18 Oct - 19 Oct
Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible
Coffee/tea maker, fridge, microwave, oven

17. 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, (25 reviews)
"Such a cute property. Clean and well maintained"
United States
Martha H.
The price is AED 514
AED 1,144 total
includes taxes & fees
29 Sep - 30 Sep
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
Exterior

18. 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.
The price is AED 551
AED 882 total
includes taxes & fees
29 Sep - 30 Sep
The Budd-Pafford House - The Exploration Suite
Terrace/patio

19. 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.
The price is AED 459
AED 781 total
includes taxes & fees
29 Sep - 30 Sep
The Budd-Pafford House: The Rose Room
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

Red Roof Inn & Suites Thomasville

Red Roof Inn & Suites Thomasville

8/10 Good
"Staff was friendly and room was clean enough. Was only there to sleep so I didn’t notice much."
ermitha 2-night trip
Posted 8 hours ago
Red Roof Inn & Suites Thomasville

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.