Holiday Rentals in Boston

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Holiday Rentals in Boston

Camellia Cottage - wheelchair friendly
10.0 out of 10, Exceptional, (4)
"Great, great place! I highly recommend when you are in the area!"
Camellia Cottage - wheelchair friendly
An elegant waterside retreat in the Red Hills
9.8 out of 10, Exceptional, (23)
"Wonderful place for a quick, quiet getaway."
The price is €260
includes taxes & fees
19 Oct - 20 Oct
An elegant waterside retreat in the Red Hills
Mimosa Getaway - Less than 1 mile from Downtown
2.0 star property
9.6 out of 10, Exceptional, (8)
"Great place to stay , clean, kids loved the bunk beds, much better than a hotel, enjoyed it"
The price is €290
includes taxes & fees
20 Oct - 21 Oct
Mimosa Getaway - Less than 1 mile from Downtown
Mimosa Cottage - Near Downtown 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!"
The price is €259
includes taxes & fees
20 Oct - 21 Oct
Mimosa Cottage - Near Downtown Thomasville
Cottage 229 - Downtown Historic Thomasville Getaway
2.0 star property
10.0 out of 10, Exceptional, (8)
"Perfect location and accommodations. Relaxing and goes perfectly with the charm of Thomasville. Will stay again. "
The price is €302
includes taxes & fees
19 Oct - 20 Oct
Cottage 229 - Downtown Historic Thomasville Getaway
Charming 2-bedroom cottage built with children and pets in mind.
2.0 star property
9.0 out of 10, Wonderful, (2)
"Cute layout. Would be perfect for 2 couples. Host was great."
The price is €267
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom cottage built with children and pets in mind.
Dog friendly nature preserve Monticello, FL
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."
The price is €187
includes taxes & fees
15 Nov - 16 Nov
Dog friendly nature preserve Monticello, FL
Sprawling Updated Ranch with Fireplace on Wimbledon
2.0 star property
9.4 out of 10, Exceptional, (8)
"The house was very clean and up to date! Really enjoyed the stay!"
The price is €297
includes taxes & fees
19 Oct - 20 Oct
Sprawling Updated Ranch with Fireplace on Wimbledon
Modern Home Near Downtown Thomasville
10.0 out of 10, Exceptional, (24)
"Nicole was very accommodating and the house was lovely. Great stay!"
The price is €286
includes taxes & fees
19 Oct - 20 Oct
Modern Home Near Downtown Thomasville
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
9.8 out of 10, Exceptional, (6)
"Great place"
The price is €311
includes taxes & fees
27 Oct - 28 Oct
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
10.0 out of 10, Exceptional, (48)
"Stayed here for my son’s graduation from FSU and it worked out well. "
The price is €280
includes taxes & fees
9 Nov - 10 Nov
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.
10.0 out of 10, Exceptional, (1)
"House was clean and exactly as described. Host was prompt with replies. House was 2 minutes from downtown thomasville.If we need to stay in thomasville again, would not hesitate to stay here again."
The price is €216
includes taxes & fees
27 Oct - 28 Oct
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.
The Roost - Downtown Thomasville
10.0 out of 10, Exceptional, (13)
"Great location in downtown. Nice & clean. "
The price is €237
includes taxes & fees
19 Oct - 20 Oct
The Roost - Downtown Thomasville
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
9.2 out of 10, Wonderful, (20)
"Large house, with beautiful back yard. "
The price is €309
includes taxes & fees
19 Oct - 20 Oct
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
The Budd-Pafford House - The Exploration Suite
9.0 out of 10, Wonderful, (9)
"Spent a very chilly weekend at this beautiful home. Neighborhood was picturesque & full of history. Resident hosts were very attentive & friendly. We felt very welcome"
The Budd-Pafford House - The Exploration Suite
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
10.0 out of 10, Exceptional, (15)
"One of the best vacation rentals I have ever had the pleasure of renting."
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
10.0 out of 10, Exceptional, (124)
"Well stocked, cute house in the best location. This was our second stay at one of the hosts properties. She is wonderful. Looking forward to staying next time."
The price is €310
includes taxes & fees
19 Oct - 20 Oct
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
SOUTHERN CHARM (Kid’s Bunk Room!)
10.0 out of 10, Exceptional, (73)
"Property was very clean and cool! "
The price is €305
includes taxes & fees
16 Oct - 17 Oct
SOUTHERN CHARM (Kid’s Bunk Room!)
Treehouse views in Historic Downtown Thomasville, Georgia
The price is €317
includes taxes & fees
16 Oct - 17 Oct
Treehouse views in Historic Downtown Thomasville, Georgia
Newly Built, Stunning 4BR/2BA with Waterfront Views
10.0 out of 10, Exceptional, (12)
"Great place to stay and good people to deal with. "
The price is €393
includes taxes & fees
27 Oct - 28 Oct
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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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 €187 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?

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks: This holiday home rental outside of Boston offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable 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?

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.