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Boston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Boston vacation rentals

Living area

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.
$334 nightly
The price is $357
Sep 16 - Sep 17
Total with taxes and fees
Sprawling Updated Ranch with Fireplace on Wimbledon
Room

2. 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
$288 nightly
The price is $308
Oct 6 - Oct 7
Total with taxes and fees
Mimosa Cottage - Near Downtown Thomasville
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.
$288 nightly
The price is $308
Sep 16 - Sep 17
Total with taxes and fees
An elegant waterside retreat in the Red Hills
Outdoor dining

4. 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.
$309 nightly
The price is $332
Sep 16 - Sep 17
Total with taxes and fees
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Living area

5. The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (33 reviews)
"Amazing location and charming loft. We loved our stay!"
United States
Katie P.
$255 nightly
The price is $272
Sep 20 - Sep 21
Total with taxes and fees
The Roost - Downtown Thomasville
Private kitchen

6. 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
$328 nightly
The price is $352
Sep 20 - Sep 21
Total with taxes and fees
Newly Built, Stunning 4BR/2BA with Waterfront Views
Private kitchen

7. 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.
$323 nightly
The price is $345
Sep 20 - Sep 21
Total with taxes and fees
Mimosa Getaway - Less than 1 mile from Downtown
Living area

8. 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.
$317 nightly
The price is $339
Sep 20 - Sep 21
Total with taxes and fees
Mimosa Stay Cottage - Thomasville Close to all the Charm
Private kitchen

9. Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (63 reviews)
"This property was in a wonderful location"
United States
Cornelia D.
$325 nightly
The price is $348
Oct 13 - Oct 14
Total with taxes and fees
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Private kitchen

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.
$376 nightly
The price is $402
Oct 14 - Oct 15
Total with taxes and fees
Modern Home Near Downtown Thomasville
Exterior detail

11. 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.
$225 nightly
The price is $262
Oct 6 - Oct 7
Total with taxes and fees
Whispering Pines Court in Historical Thomasville
Private kitchen

12. Sage Cottage I Walk to Downtown

Sage Cottage I Walk to Downtown
Thomasville
9.8 out of 10, Exceptional, (12 reviews)
"Property was perfect. Great location, super cute and clean. We enjoyed our stay & great communication with host. "
United States
Rosemary H.
$307 nightly
The price is $355
Sep 16 - Sep 17
Total with taxes and fees
Sage Cottage I Walk to Downtown
Exterior detail

13. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (144 reviews)
"This was my 2nd stay at Quail Cottage. Highly recommend! "
United States
Misti B.
$306 nightly
The price is $354
Sep 16 - Sep 17
Total with taxes and fees
QUAIL COTTAGE - Downtown Thomasville!
Private kitchen

14. 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.
$410 nightly
The price is $440
Sep 30 - Oct 1
Total with taxes and fees
Southern Charm Home: Pool + Fireplace + Large Yard
Private kitchen

15. 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.
$350 nightly
The price is $374
Sep 20 - Sep 21
Total with taxes and fees
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Interior

16. 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 17 - Sep 18
Total with taxes and fees
Dog friendly nature preserve Monticello, FL
Interior

17. The Walcott Cottage: Walkable Historic Retreat in Thomasville

The Walcott Cottage: Walkable Historic Retreat in Thomasville
Dawson Street Historic District
$344 nightly
The price is $368
Sep 20 - Sep 21
Total with taxes and fees
The Walcott Cottage: Walkable Historic Retreat in Thomasville
Living area

18. 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 21 - Sep 22
Total with taxes and fees
The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11
Dining

19. 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.
$346 nightly
The price is $402
Sep 16 - Sep 17
Total with taxes and fees
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Terrace/patio

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, (21 reviews)
"Cute house in great location. "
United States
Dan L.
$197 nightly
The price is $215
Sep 28 - Sep 29
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

Home2 Suites By Hilton Thomasville

Home2 Suites By Hilton Thomasville

10/10 Excellent
"Excellent stay, wife was not pleased with the lighting in bathroom. Excellent breakfast and friendly staff."
David 2-night trip
Posted 2 days 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?

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 Sweet Grass Dairy Marketplace, Thomasville's Historic Big Oak, and Pebble Hill Plantation. In the larger area, you’ll find Lapham-Patterson House 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.