Boston Holiday Rentals

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Holiday Rentals in Boston

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

10.0 out of 10, Exceptional, (46)
"Stayed here for my son’s graduation from FSU and it worked out well. "
The price is AU$469
includes taxes & fees
6 Oct - 7 Oct
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Cottage On Park Ave. Off-season pricing.

10.0 out of 10, Exceptional, (185)
"For us this cottage was perfect. Clean, good set up, perfect for a couple. Pet friendly. It is a great spot and we will be back for sure. "
Cottage On Park Ave. Off-season pricing.

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 AU$540
includes taxes & fees
5 Oct - 6 Oct
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

Sprawling Updated Ranch with Fireplace on Wimbledon

2.0 star property
9.4 out of 10, Exceptional, (8)
"The property was very comfortable. It is located in a great area. Overall we a great stay. The weather was raining we didn't get to go out in beautiful yard."
The price is AU$518
includes taxes & fees
5 Oct - 6 Oct
Sprawling Updated Ranch with Fireplace on Wimbledon

SOUTHERN CHARM (Kid’s Bunk Room!)

10.0 out of 10, Exceptional, (70)
"Property was very clean and cool! "
The price is AU$529
includes taxes & fees
7 Oct - 8 Oct
SOUTHERN CHARM (Kid’s Bunk Room!)

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 AU$453
includes taxes & fees
14 Oct - 15 Oct
Charming 2-bedroom cottage built with children and pets in mind.

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

10.0 out of 10, Exceptional, (124)
"This bungalow is located conveniently to everything. It was comfortable and quiet. The hostess was extremely friendly and helpful. A definite A for a visit to Thomasville."
The price is AU$541
includes taxes & fees
5 Oct - 6 Oct
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

Mimosa Cottage - Near Downtown Thomasville

9.8 out of 10, Exceptional, (8)
"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 AU$447
includes taxes & fees
5 Oct - 6 Oct
Mimosa Cottage - Near Downtown Thomasville

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

10.0 out of 10, Exceptional, (43)
"Great home, beautiful location! Very easy to get to downtown. We especially loved the back deck with peaceful sounds of nature! Sheri was very helpful and a gracious hostess!"
The Quail's Nest! Convenient to downtown, quiet and fully remodeled!

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 AU$691
includes taxes & fees
5 Oct - 6 Oct
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

The Roost - Downtown Thomasville

10.0 out of 10, Exceptional, (13)
"Great property and location. Would highly recommend"
The price is AU$404
includes taxes & fees
12 Oct - 13 Oct
The Roost - Downtown Thomasville

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

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

The price is AU$1,049
includes taxes & fees
6 Oct - 7 Oct
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

Hayden's Getaway: Sleep 6, Charming & Spacious

9.0 out of 10, Wonderful, (9)
"Great place away from noise but close enough to restaurants and other needs"
Hayden's Getaway: Sleep 6, Charming & Spacious

Georgia Blue Cottage

9.2 out of 10, Wonderful, (14)
"Great for 6 adults."
Georgia Blue Cottage

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 AU$304
includes taxes & fees
6 Oct - 7 Oct
Camellia Cottage - wheelchair friendly

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 AU$324
includes taxes & fees
31 Oct - 1 Nov
Dog friendly nature preserve Monticello, FL

The Budd-Pafford House - The Exploration Suite

8.8 out of 10, Excellent, (8)
"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 price is AU$376
includes taxes & fees
14 Oct - 15 Oct
The Budd-Pafford House - The Exploration Suite

BuckHaven Countryside Retreat with Fishing Pond

9.8 out of 10, Exceptional, (7)
"My second time stating here with friends. Just as good the second time as the first. "
BuckHaven Countryside Retreat with Fishing Pond

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 AU$500
includes taxes & fees
5 Oct - 6 Oct
Mimosa Getaway - Less than 1 mile from Downtown
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, 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$304 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?

Newly Renovated - Thomasville Getaway - Large Fenced Backyard: This holiday home rental outside of Boston is located in the city centre, and has a patio, a selection of games and a BBQ to put you at ease 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.