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Boston Holiday Rentals

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Our top choices for Boston holiday rentals

1. 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
The price is AU$426
includes taxes & fees
1 Sept - 2 Sept
Mimosa Cottage - Near Downtown Thomasville

2. 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.
The price is AU$433
includes taxes & fees
30 Aug - 31 Aug
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

3. 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.
The price is AU$510
includes taxes & fees
30 Aug - 31 Aug
Sprawling Updated Ranch with Fireplace on Wimbledon

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.
The price is AU$499
includes taxes & fees
30 Aug - 31 Aug
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

5. The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (31 reviews)
"Amazing location and charming loft. We loved our stay!"
United States
Katie P.
The price is AU$377
includes taxes & fees
30 Aug - 31 Aug
The Roost - Downtown Thomasville

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, (6 reviews)
"Great location spacious layout furnished perfectly "
United States
Damian Ray V.
The price is AU$467
includes taxes & fees
30 Aug - 31 Aug
Mimosa Stay Cottage - Thomasville Close to all the Charm

7. 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 AU$382
includes taxes & fees
31 Aug - 1 Sept
Whispering Pines Court in Historical Thomasville

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
The price is AU$510
includes taxes & fees
30 Aug - 31 Aug
Newly Built, Stunning 4BR/2BA with Waterfront Views

9. 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.
The price is AU$475
includes taxes & fees
30 Aug - 31 Aug
Mimosa Getaway - Less than 1 mile from Downtown

10. 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 AU$423
includes taxes & fees
1 Sept - 2 Sept
An elegant waterside retreat in the Red Hills

11. 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.
The price is AU$489
includes taxes & fees
30 Aug - 31 Aug
Sage Cottage I Walk to Downtown

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 AU$303
includes taxes & fees
28 Aug - 29 Aug
Dog friendly nature preserve Monticello, FL

13. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (143 reviews)
"This was my 2nd stay at Quail Cottage. Highly recommend! "
United States
Misti B.
The price is AU$481
includes taxes & fees
16 Sept - 17 Sept
QUAIL COTTAGE - Downtown Thomasville!

14. Treehouse views in Historic Downtown Thomasville, Georgia

Treehouse views in Historic Downtown Thomasville, Georgia
Thomasville
10.0 out of 10, Exceptional, (10 reviews)
"Great location, very comfortable and charming home."
United States
Betsy H.
The price is AU$523
includes taxes & fees
6 Sept - 7 Sept
Treehouse views in Historic Downtown Thomasville, Georgia

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, (33 reviews)
"We loved the location and enjoyed the back yard."
United States
Grace F.
The price is AU$510
includes taxes & fees
30 Aug - 31 Aug
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

16. The Walcott Cottage: Walkable Historic Retreat in Thomasville

The Walcott Cottage: Walkable Historic Retreat in Thomasville
Dawson Street Historic District
The price is AU$504
includes taxes & fees
30 Aug - 31 Aug
The Walcott Cottage: Walkable Historic Retreat in Thomasville

17. 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.
The price is AU$629
includes taxes & fees
31 Aug - 1 Sept
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

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

The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11
Thomasville
The price is AU$374
includes taxes & fees
31 Aug - 1 Sept
The 1886 House Historic Downtown Thomasville 4 bedroom, sleeps 11

19. 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)
"The Schoolhouse was comfortable, stylish and very clean. It had everything we needed for a wonderful stay. We hope to return one day!"
United States
Heather S.
The price is AU$452
includes taxes & fees
29 Aug - 30 Aug
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

20. The Mash Manor

The Mash Manor
Dawson Street Historic District
9.0 out of 10, Wonderful, (30 reviews)
"Perfect place for our group of 5! Everyone had their own bedroom and bath and the house was spacious and just beautiful! We loved the quick walk to downtown Thomasville and all the holiday festivities. The owner was very responsive and helpful as well. "
United States
Debra B.
The price is AU$957
includes taxes & fees
30 Aug - 31 Aug
The Mash Manor
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, 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 favourite 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 depend 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 AU$310 per night. Entering your travel dates in the search wizard might find you 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?

Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville: This holiday home rental outside of Boston is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. 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 Thomasville Genealogical, History and Fine Arts Library.

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.