Boston Holiday Rentals

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Our top choices for Boston holiday rentals

Modern Home Near Downtown Thomasville

Modern Home Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (28 reviews)
"Great stay!!! Property was very clean and well maintained. Exceeded our expectations and made our visit so much more enjoyable. Highly recommend and would book again when visiting in town."
United States
Stephanie S.
The price is NZ$602
includes taxes & fees
2 Mar - 3 Mar
Modern Home Near Downtown Thomasville

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

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Thomasville
9.8 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Michael S.
The price is NZ$578
includes taxes & fees
8 Feb - 9 Feb
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

An elegant waterside retreat in the Red Hills

An elegant waterside retreat in the Red Hills
Thomasville
9.8 out of 10, Exceptional, (24 reviews)
"Was absolutely amazing we will be comin back for sure!!! So peaceful just perfect "
United States
brittiny c.
The price is NZ$504
includes taxes & fees
8 Feb - 9 Feb
An elegant waterside retreat in the Red Hills

Mimosa Getaway - Less than 1 mile from Downtown

Mimosa Getaway - Less than 1 mile from Downtown
Thomasville
9.6 out of 10, Exceptional, (12 reviews)
"Clean, convenient location, and easy check in."
United States
Emily H.
The price is NZ$533
includes taxes & fees
4 Feb - 5 Feb
Mimosa Getaway - Less than 1 mile from Downtown

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, (16 reviews)
"Clean great location and very friendly thank you for the stay we will be back"
United States
ROBERT B.
The price is NZ$531
includes taxes & fees
5 Feb - 6 Feb
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

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, (1 review)
"Great location spacious layout furnished perfectly "
United States
Damian Ray V.
The price is NZ$532
includes taxes & fees
18 Feb - 19 Feb
Mimosa Stay Cottage - Thomasville Close to all the Charm

The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Very convenient and super close to everything in downtown Thomasville. "
United States
Lisa L.
The price is NZ$443
includes taxes & fees
4 Feb - 5 Feb
The Roost - Downtown Thomasville

Mimosa Cottage - Near Downtown Thomasville

Mimosa Cottage - Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (13 reviews)
"Great location"
United States
Landon W.
The price is NZ$475
includes taxes & fees
8 Feb - 9 Feb
Mimosa Cottage - Near Downtown Thomasville

SOUTHERN CHARM (Kid’s Bunk Room!)

SOUTHERN CHARM (Kid’s Bunk Room!)
Thomasville
10.0 out of 10, Exceptional, (77 reviews)
"Wonderful stay would love to stay again!"
United States
Lakeisa C.
The price is NZ$565
includes taxes & fees
4 Feb - 5 Feb
SOUTHERN CHARM (Kid’s Bunk Room!)

Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.6 out of 10, Exceptional, (15 reviews)
"The house was very clean and up to date! Really enjoyed the stay!"
United States
Sondra A.
The price is NZ$619
includes taxes & fees
8 Feb - 9 Feb
Sprawling Updated Ranch with Fireplace on Wimbledon

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

Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Thomasville
9.4 out of 10, Exceptional, (27 reviews)
"Very comfortable place to stay when visiting Thomasville! "
United States
Sarah S.
The price is NZ$599
includes taxes & fees
4 Feb - 5 Feb
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

Cottage 229 - Downtown Historic Thomasville Getaway

Cottage 229 - Downtown Historic Thomasville Getaway
Thomasville
10.0 out of 10, Exceptional, (13 reviews)
"We loved the home! Everything we needed was there for us and the location was perfect. Would love to stay here again!"
United States
emily h.
The price is NZ$582
includes taxes & fees
11 Feb - 12 Feb
Cottage 229 - Downtown Historic Thomasville Getaway

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

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
10.0 out of 10, Exceptional, (12 reviews)
"Great place to stay and good people to deal with. "
United States
RYAN H.
The price is NZ$768
includes taxes & fees
3 Mar - 4 Mar
Newly Built, Stunning 4BR/2BA with Waterfront Views

Treehouse views in Historic Downtown Thomasville, Georgia

Treehouse views in Historic Downtown Thomasville, Georgia
Thomasville
10.0 out of 10, Exceptional, (5 reviews)
"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 NZ$629
includes taxes & fees
4 Feb - 5 Feb
Treehouse views in Historic Downtown Thomasville, Georgia

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, (5 reviews)
"Nicely equipped kitchen , great areas to relax and very quiet "
United States
Jesse V.
The price is NZ$1,108
includes taxes & fees
4 Feb - 5 Feb
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

Southern Charm Home: Pool + Fireplace + Large Yard

Southern Charm Home: Pool + Fireplace + Large Yard
Thomasville
10.0 out of 10, Exceptional, (1 review)
"Convenient location and has everything you need."
United States
Dee J.
The price is NZ$691
includes taxes & fees
8 Feb - 9 Feb
Southern Charm Home: Pool + Fireplace + Large Yard

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (134 reviews)
"Great location "
United States
Misti
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

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, (6 reviews)
"Very beautiful property and well maintained with southern charm. "
United States
Rebecca N.
The price is NZ$738
includes taxes & fees
4 Feb - 5 Feb
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

The Mash Manor

The Mash Manor
Dawson Street Historic District
9.2 out of 10, Wonderful, (27 reviews)
"The house was very clean. Plenty of room for my family. Great location to shops and restaurants. Plenty of parking. "
United States
Pat S.
The price is NZ$1,055
includes taxes & fees
9 Feb - 10 Feb
The Mash Manor
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 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 NZ$443 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.