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Our top choices for Boston holiday rentals

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 £276
includes taxes & fees
27 Sept - 28 Sept
Sprawling Updated Ranch with Fireplace on Wimbledon

2. 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 £261
includes taxes & fees
28 Sept - 29 Sept
Mimosa Getaway - Less than 1 mile from Downtown

3. 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 £296
includes taxes & fees
25 Oct - 26 Oct
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

4. 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 £277
includes taxes & fees
28 Sept - 29 Sept
Newly Built, Stunning 4BR/2BA with Waterfront Views

5. 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 £165
includes taxes & fees
27 Sept - 28 Sept
Dog friendly nature preserve Monticello, FL

6. 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 £233
includes taxes & fees
5 Oct - 6 Oct
Mimosa Cottage - Near Downtown Thomasville

7. The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (37 reviews)
"Amazing location and charming loft. We loved our stay!"
United States
Katie P.
The price is £209
includes taxes & fees
27 Sept - 28 Sept
The Roost - Downtown Thomasville

8. 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 £253
includes taxes & fees
7 Oct - 8 Oct
Whispering Pines Court in Historical Thomasville

9. 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 £257
includes taxes & fees
27 Sept - 28 Sept
Mimosa Stay Cottage - Thomasville Close to all the Charm

10. 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.
Sage Cottage I Walk to Downtown

11. 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 £230
includes taxes & fees
28 Sept - 29 Sept
An elegant waterside retreat in the Red Hills

12. 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 £263
includes taxes & fees
25 Oct - 26 Oct
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

13. 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 £263
includes taxes & fees
14 Oct - 15 Oct
Modern Home Near Downtown Thomasville

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.
The price is £325
includes taxes & fees
29 Sept - 30 Sept
Southern Charm Home: Pool + Fireplace + Large Yard

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.
The price is £278
includes taxes & fees
27 Sept - 28 Sept
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

16. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (145 reviews)
"Very nice home. Communication was excellent! We would stay here again."
United States
colleen z.
The price is £271
includes taxes & fees
6 Oct - 7 Oct
QUAIL COTTAGE - Downtown Thomasville!

17. 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.
The price is £169
includes taxes & fees
18 Oct - 19 Oct
Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible

18. 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 £282
includes taxes & fees
27 Sept - 28 Sept
The Walcott Cottage: Walkable Historic Retreat in Thomasville

19. 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, (1 review)
"Great experience. This sweet older home was very comfortable and clean. I loved the little extras like make-up wipes, bandaids, hair dryers, coffee, etc. I would definitely stay here agin. Thank you for a fantastic experience."
United States
Sarah M.
The price is £202
includes taxes & fees
4 Oct - 5 Oct
The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11

20. 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, (6 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 £241
includes taxes & fees
25 Oct - 26 Oct
New!! Remodeled downtown home. Golf cart available to rent. Walk to Broad St.
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

Find out more about Boston

Everything you need to know about Boston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Boston holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Boston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Boston holiday rentals we have selected for you start as low as £165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston holiday 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 holiday.

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 holiday rentals in Boston?

Yes, there are holiday rentals close to the most popular sights in Boston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Boston has to offer?

Sprawling Updated Ranch with Fireplace on Wimbledon: This holiday home rental outside of Boston is located in the city centre, and has a patio, a selection of games and a BBQ 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 that 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 wider area, you’ll find Sweet Grass Dairy Marketplace and Jack Hadley Black History Museum.

What’s a holiday rental in Boston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Boston. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.