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Boston Holiday Rentals

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Our top choices for Boston holiday rentals

1. Dog friendly nature preserve Monticello, FL

Dog friendly nature preserve Monticello, FL
Monticello
10.0 out of 10, Exceptional, (2 reviews)
"Nice rustic environment and very pet friendly."
United States
Jeff B.
The price is NZ$361
includes taxes & fees
10 Sept - 11 Sept
Dog friendly nature preserve Monticello, FL

2. 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 NZ$361
includes taxes & fees
9 Sept - 10 Sept
The Budd-Pafford House: The Rose Room

3. 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 NZ$411
includes taxes & fees
10 Sept - 11 Sept
The Budd-Pafford House - The Exploration Suite

4. Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible

Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible
Monticello
9.6 out of 10, Exceptional, (19 reviews)
"Cute house in great location. "
United States
Dan L.
The price is NZ$370
includes taxes & fees
16 Aug - 17 Aug
Summer and Early Fall Special Rates Camellia Cottage - Wheelchair Accessible

5. 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 NZ$545
includes taxes & fees
13 Aug - 14 Aug
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

6. 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 NZ$602
includes taxes & fees
17 Aug - 18 Aug
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

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

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
9.8 out of 10, Exceptional, (20 reviews)
"The property was clean and spacious for our family. The access were very easy."
United States
Frederick E
The price is NZ$633
includes taxes & fees
17 Aug - 18 Aug
Newly Built, Stunning 4BR/2BA with Waterfront Views

8. Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.8 out of 10, Exceptional, (21 reviews)
"Was a very comfortable home for our girl’s trip of 5 ladies! "
United States
Julia N.
The price is NZ$633
includes taxes & fees
17 Aug - 18 Aug
Sprawling Updated Ranch with Fireplace on Wimbledon

9. 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 NZ$459
includes taxes & fees
31 Aug - 1 Sept
Whispering Pines Court in Historical Thomasville

10. Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
Thomasville
10.0 out of 10, Exceptional, (12 reviews)
"Nicely equipped kitchen , great areas to relax and very quiet "
United States
Jesse V.
The price is NZ$1,108
includes taxes & fees
17 Aug - 18 Aug
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

11. 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 NZ$700
includes taxes & fees
25 Aug - 26 Aug
Treehouse views in Historic Downtown Thomasville, Georgia

12. Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (62 reviews)
"Enjoyed our stay very much."
United States
Barbara F.
The price is NZ$522
includes taxes & fees
30 Aug - 31 Aug
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

13. 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 NZ$573
includes taxes & fees
16 Aug - 17 Aug
Mimosa Getaway - Less than 1 mile from Downtown

14. 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 NZ$562
includes taxes & fees
30 Aug - 31 Aug
Mimosa Stay Cottage - Thomasville Close to all the Charm

15. 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 NZ$518
includes taxes & fees
18 Aug - 19 Aug
Mimosa Cottage - Near Downtown Thomasville

16. 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, (22 reviews)
"Our stay was absolutely wonderful! Will definitely be booking here again!"
United States
Unspecified U.
The price is NZ$798
includes taxes & fees
17 Aug - 18 Aug
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

17. QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (143 reviews)
"Very nice home. Communication was excellent! We would stay here again."
United States
colleen z.
The price is NZ$588
includes taxes & fees
13 Aug - 14 Aug
QUAIL COTTAGE - Downtown Thomasville!

18. 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)
"We loved being away from the city in this secluded, quiet retreat. I was able to take some remote work meetings from the covered deck, which was such a nice change of scenery! The owners provided top notch instructions and maintained excellent communication throughout the stay. We can’t wait to come back!"
United States
Rebecca V.
The price is NZ$520
includes taxes & fees
9 Sept - 10 Sept
An elegant waterside retreat in the Red Hills

19. Charming 2-bedroom cottage built with children and pets in mind.

Charming 2-bedroom cottage built with children and pets in mind.
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 NZ$590
includes taxes & fees
16 Aug - 17 Aug
Charming 2-bedroom cottage built with children and pets in mind.

20. The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (30 reviews)
"Amazing location and charming loft. We loved our stay!"
United States
Katie P.
The price is NZ$459
includes taxes & fees
17 Aug - 18 Aug
The Roost - Downtown Thomasville
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Boston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Boston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Boston. Seeing all the best attractions is bound to make you fall in love with Boston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Boston short-term rentals, that won’t be hard to do.

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?

QUAIL COTTAGE - Downtown Thomasville!: This holiday home rental outside of Boston is located in the city centre, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Boston?

Explore the area and family-friendly sights such as Sweet Grass Dairy Marketplace, or get out into nature at a spot like Thomasville Rose Garden. In the wider area, you’ll find Thomasville's Historic Big Oak and Pebble Hill Plantation.

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.