Boston Holiday Rentals

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Holiday Rentals in Boston

Cottage 229 - Downtown Historic Thomasville Getaway

2.0 star property
Thomasville
10.0 out of 10, Exceptional, (11)
"Perfect location and accommodations. Relaxing and goes perfectly with the charm of Thomasville. Will stay again. "
United States
Michelle B.
The price is AU$552
includes taxes & fees
2 Dec - 3 Dec
Cottage 229 - Downtown Historic Thomasville Getaway

Camellia Cottage - wheelchair friendly

Monticello
10.0 out of 10, Exceptional, (8)
"Great location, clean, and comfortable. "
United States
Teresa
The price is AU$314
includes taxes & fees
7 Dec - 8 Dec
Camellia Cottage - wheelchair friendly

Cozy studio in a vintage 1930’s Gulf Gas Station in charming Thomasville GA

Downtown Historic District
10.0 out of 10, Exceptional, (2)
"It was great to be within walking distance to downtown Thomasville."
United States
Gina L.
The price is AU$281
includes taxes & fees
7 Dec - 8 Dec
Cozy studio in a vintage 1930’s Gulf Gas Station in charming Thomasville GA

Sprawling Updated Ranch with Fireplace on Wimbledon

2.0 star property
Thomasville
9.4 out of 10, Exceptional, (10)
"The house was very clean and up to date! Really enjoyed the stay!"
United States
Sondra A.
The price is AU$540
includes taxes & fees
1 Dec - 2 Dec
Sprawling Updated Ranch with Fireplace on Wimbledon

Mimosa Cottage - Near Downtown Thomasville

Thomasville
9.8 out of 10, Exceptional, (9)
"This was a very nice property. It had everything you need for a comfortable stay! The owners were also very easy to get ahold of. Thank you for a nice stay!"
United States
Catherine
The price is AU$452
includes taxes & fees
30 Nov - 1 Dec
Mimosa Cottage - Near Downtown Thomasville

Mimosa Getaway - Less than 1 mile from Downtown

2.0 star property
Thomasville
9.4 out of 10, Exceptional, (9)
"Everything was just as described. Not too far from town. Love the back yard space. Only needed to contact someone once with a question and they were quick to respond. Will definitely stay there again. "
United States
Amy S.
The price is AU$511
includes taxes & fees
8 Dec - 9 Dec
Mimosa Getaway - Less than 1 mile from Downtown

Treehouse views in Historic Downtown Thomasville, Georgia

Thomasville
10.0 out of 10, Exceptional, (2)
"Great location near downtown. I chose this spot because of the nice check in,/ check out times (3 & 11). Recommend!"
United States
Michael B.
The price is AU$560
includes taxes & fees
7 Dec - 8 Dec
Treehouse views in Historic Downtown Thomasville, Georgia

Modern Home Near Downtown Thomasville

Thomasville
10.0 out of 10, Exceptional, (28)
"Nicole was very accommodating and the house was lovely. Great stay!"
United States
Jack D.
The price is AU$512
includes taxes & fees
1 Dec - 2 Dec
Modern Home Near Downtown Thomasville

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

Thomasville
9.8 out of 10, Exceptional, (7)
"Great place"
United States
Michael S.
The price is AU$555
includes taxes & fees
9 Dec - 10 Dec
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.

Thomasville
10.0 out of 10, Exceptional, (4)
"The place was clean and beautiful! I felt safe there, thank you!"
United States
Sabrina S.
The price is AU$392
includes taxes & fees
5 Dec - 6 Dec
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.

Dog friendly nature preserve Monticello, FL

Monticello
10.0 out of 10, Exceptional, (1)
"Quiet and relaxing spot. Very well maintained and clean. Wonderful hosts. My only regret is that we couldn't stay longer."
United States
KARL L.
Dog friendly nature preserve Monticello, FL

An elegant waterside retreat in the Red Hills

Thomasville
9.8 out of 10, Exceptional, (24)
"Very nice property. Good amenities. Keurig didn’t work well, no good directions fot direct tv. Cabin very clean, wonderful setting at end of gravel road. Great wildlife, including the mouse which came to visit. Recommend highly. "
United States
michael
The price is AU$459
includes taxes & fees
30 Nov - 1 Dec
An elegant waterside retreat in the Red Hills

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

2.0 star property
Thomasville
9.6 out of 10, Exceptional, (4)
"We enjoyed our stay in Thomasville! The beds were comfortable, everything was clean and my dogs especially loved the court yard area. It was in walking distance to downtown which we loved. Would definitely stay here again! "
United States
Lindsey J.
The price is AU$421
includes taxes & fees
8 Dec - 9 Dec
Charming 2-bedroom cottage built with children and pets in mind.

Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

Monticello
10.0 out of 10, Exceptional, (15)
"Clean great location and very friendly thank you for the stay we will be back"
United States
ROBERT B.
The price is AU$508
includes taxes & fees
5 Dec - 6 Dec
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

Thomasville
10.0 out of 10, Exceptional, (129)
"Great location "
United States
Misti
The price is AU$548
includes taxes & fees
30 Nov - 1 Dec
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Thomasville
10.0 out of 10, Exceptional, (52)
"Stayed here for my son’s graduation from FSU and it worked out well. "
United States
Jana H.
The price is AU$486
includes taxes & fees
14 Dec - 15 Dec
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

Thomasville
10.0 out of 10, Exceptional, (5)
"Host was welcoming and thoughtful. Home was clean and beautifully decorated. Very comfortable, we would definitely stay here again. "
United States
Teresa M.
The price is AU$701
includes taxes & fees
30 Nov - 1 Dec
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

Southern Charm Home: Pool + Fireplace + Large Yard

Thomasville
10.0 out of 10, Exceptional, (1)
"Convenient location and has everything you need."
United States
Dee J.
The price is AU$659
includes taxes & fees
1 Dec - 2 Dec
Southern Charm Home: Pool + Fireplace + Large Yard

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

Thomasville
10.0 out of 10, Exceptional, (4)
"Nicely equipped kitchen , great areas to relax and very quiet "
United States
Jesse V.
The price is AU$1,073
includes taxes & fees
1 Dec - 2 Dec
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

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

Thomasville
10.0 out of 10, Exceptional, (12)
"Beautiful house, great location, great value!"
United States
DEANNA B.
The price is AU$711
includes taxes & fees
9 Dec - 10 Dec
Newly Built, Stunning 4BR/2BA with Waterfront Views
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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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$281 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?

2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.: This holiday home rental outside of Boston has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.