Holiday Rentals in Boston

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Holiday Rentals in Boston

Cottage On Park Ave. Off-season pricing.

10.0 out of 10, Exceptional, (180)
"Secluded and enjoyable. More comfortable than any hotel."
Cottage On Park Ave. Off-season pricing.

SOUTHERN CHARM (Kid’s Bunk Room!)

10.0 out of 10, Exceptional, (69)
"We had a great stay. Everything was clean and very nice. We love Thomasville! This VRBO is in a great location. "
The price is €307
includes taxes & fees
1 Sept - 2 Sept
SOUTHERN CHARM (Kid’s Bunk Room!)

The Mash Manor

9.2 out of 10, Wonderful, (21)
"The home was beautiful, clean and in a perfect walkable location to downtown and the Big Oak tree."
The price is €545
includes taxes & fees
1 Sept - 2 Sept
The Mash Manor

The Roost - Downtown Thomasville

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay at The Roost. The location is perfect for exploring and enjoying downtown Thomasville and the surrounding area. Thank you."
The price is €230
includes taxes & fees
9 Sept - 10 Sept
The Roost - Downtown Thomasville

Camellia Cottage - wheelchair friendly

10.0 out of 10, Exceptional, (4)
"Great, great place! I highly recommend when you are in the area!"
The price is €169
includes taxes & fees
29 Sept - 30 Sept
Camellia Cottage - wheelchair friendly

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

The price is €611
includes taxes & fees
8 Sept - 9 Sept
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

10.0 out of 10, Exceptional, (45)
"Stayed here for my son’s graduation from FSU and it worked out well. "
The price is €272
includes taxes & fees
1 Sept - 2 Sept
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Charming 1-bedroom house in Metcalfe with modern amenities and a vintage vibe

10.0 out of 10, Exceptional, (8)
"Excellent stay!"
The price is €153
includes taxes & fees
4 Sept - 5 Sept
Charming 1-bedroom house in Metcalfe with modern amenities and a vintage vibe

Secluded pool home on 4+ acres

10.0 out of 10, Exceptional, (23)
"Property was very nice host/owner is very easy to work with and helped us a lot with our stay. "
Secluded pool home on 4+ acres

Newly Updated-Sprawling Ranch on Wimbledon

2.0 star property
9.4 out of 10, Exceptional, (8)
"The property was perfect for the occasion "
The price is €309
includes taxes & fees
1 Sept - 2 Sept
Newly Updated-Sprawling Ranch on Wimbledon

The Quail's Nest! Convenient to downtown, quiet and fully remodeled!

10.0 out of 10, Exceptional, (43)
"Very quiet neighborhood and comfortable home!"
The Quail's Nest! Convenient to downtown, quiet and fully remodeled!

Victoria's Secret Cottage (Downtown Thomasville) New Contrusction

10.0 out of 10, Exceptional, (35)
"We really enjoyed our stay here. "
Victoria's Secret Cottage (Downtown Thomasville) New Contrusction

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

10.0 out of 10, Exceptional, (9)
"Great place to stay and good people to deal with. "
The price is €366
includes taxes & fees
9 Sept - 10 Sept
Newly Built, Stunning 4BR/2BA with Waterfront Views

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

10.0 out of 10, Exceptional, (11)
"Wonderful house- beautiful updates, clean, comfortable and had everything we needed! "
The price is €285
includes taxes & fees
1 Sept - 2 Sept
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

Mimosa Getaway - Less than 1 mile from Downtown

2.0 star property
9.6 out of 10, Exceptional, (7)
"Great place to stay , clean, kids loved the bunk beds, much better than a hotel, enjoyed it"
The price is €288
includes taxes & fees
2 Sept - 3 Sept
Mimosa Getaway - Less than 1 mile from Downtown

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

10.0 out of 10, Exceptional, (2)
"Host was welcoming and thoughtful. Home was clean and beautifully decorated. Very comfortable, we would definitely stay here again. "
The price is €392
includes taxes & fees
1 Sept - 2 Sept
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

9.0 out of 10, Wonderful, (18)
"The property was clean and spacious. We really enjoyed our stay"
The price is €319
includes taxes & fees
2 Sept - 3 Sept
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

Hoodwood bed and breakfast

10.0 out of 10, Exceptional, (63)
"Quiet neighborhood, convenient to historic downtown, comfortable accommodations. Charming old home with updated amenities. Would happily stay there again!"
Hoodwood bed and breakfast

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

10.0 out of 10, Exceptional, (123)
"Great location and very clean. The communication was fantastic and we will definitely be staying here again next year!"
The price is €312
includes taxes & fees
1 Sept - 2 Sept
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

Georgia Blue Cottage

9.2 out of 10, Wonderful, (12)
"Great for 6 adults."
Georgia Blue Cottage
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

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 €153 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?

SOUTHERN CHARM (Kid’s Bunk Room!): 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. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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.