Boston Vacation Rentals

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Vacation Rentals in Boston

Interior
Camellia Cottage - wheelchair friendly
Camellia Cottage - wheelchair friendly
10.0 out of 10, Exceptional, (4)
"Great, great place! I highly recommend when you are in the area!"
United States
Darrin M.
$178 nightly
The price is $194
Oct 20 - Oct 21
Total with taxes and fees
Camellia Cottage - wheelchair friendly
TV
An elegant waterside retreat in the Red Hills
An elegant waterside retreat in the Red Hills
9.8 out of 10, Exceptional, (23)
"Wonderful place for a quick, quiet getaway."
United States
Chris Y.
$285 nightly
The price is $293
Oct 20 - Oct 21
Total with taxes and fees
An elegant waterside retreat in the Red Hills
Fridge, microwave, oven, stovetop
Mimosa Getaway - Less than 1 mile from Downtown
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"
United States
carl e.
$319 nightly
The price is $327
Oct 20 - Oct 21
Total with taxes and fees
Mimosa Getaway - Less than 1 mile from Downtown
Fridge, microwave, oven, stovetop
Mimosa Cottage - Near Downtown Thomasville
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!"
United States
Catherine
$285 nightly
The price is $292
Oct 20 - Oct 21
Total with taxes and fees
Mimosa Cottage - Near Downtown Thomasville
Fridge, microwave, oven, stovetop
Cottage 229 - Downtown Historic Thomasville Getaway
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. "
United States
Michelle B.
$341 nightly
The price is $351
Oct 20 - Oct 21
Total with taxes and fees
Cottage 229 - Downtown Historic Thomasville Getaway
Fridge, microwave, oven, stovetop
Charming 2-bedroom cottage built with children and pets in mind.
Charming 2-bedroom cottage built with children and pets in mind.
2.0 star property
9.4 out of 10, Exceptional, (3)
"Very comfortable and clean. It was almost a shame that our stay was so short. We would definitely stay here again. "
United States
Sarah M.
$261 nightly
The price is $303
Nov 3 - Nov 4
Total with taxes and fees
Charming 2-bedroom cottage built with children and pets in mind.
Exterior
Dog friendly nature preserve Monticello, FL
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."
United States
KARL L.
$200 nightly
The price is $218
Oct 31 - Nov 1
Total with taxes and fees
Dog friendly nature preserve Monticello, FL
Fridge, microwave, oven, stovetop
Sprawling Updated Ranch with Fireplace on Wimbledon
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!"
United States
Sondra A.
$330 nightly
The price is $339
Oct 20 - Oct 21
Total with taxes and fees
Sprawling Updated Ranch with Fireplace on Wimbledon
Fridge, microwave, oven, stovetop
Modern Home Near Downtown Thomasville
Modern Home Near Downtown Thomasville
10.0 out of 10, Exceptional, (25)
"Nicole was very accommodating and the house was lovely. Great stay!"
United States
Jack D.
$319 nightly
The price is $327
Oct 20 - Oct 21
Total with taxes and fees
Modern Home Near Downtown Thomasville
Fridge, microwave, oven, stovetop
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
9.8 out of 10, Exceptional, (6)
"Great place"
United States
Michael S.
$347 nightly
The price is $355
Oct 20 - Oct 21
Total with taxes and fees
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
TV, books
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
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. "
United States
Jana H.
$308 nightly
The price is $316
Nov 9 - Nov 10
Total with taxes and fees
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Property grounds
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.
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."
United States
Mike P.
$210 nightly
The price is $245
Oct 27 - Oct 28
Total with taxes and fees
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.
Interior
The Roost - Downtown Thomasville
The Roost - Downtown Thomasville
10.0 out of 10, Exceptional, (13)
"Very convenient and super close to everything in downtown Thomasville. "
United States
Lisa L.
$262 nightly
The price is $270
Oct 20 - Oct 21
Total with taxes and fees
The Roost - Downtown Thomasville
Fridge, microwave, oven, stovetop
Spacious 4BR/3BA Home with Large Fenced Yard – Near 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. "
United States
Charles H.
$330 nightly
The price is $353
Oct 20 - Oct 21
Total with taxes and fees
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Exterior
The Budd-Pafford House - The Exploration Suite
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"
United States
ASHLEY C.
$226 nightly
The price is $246
Oct 20 - Oct 21
Total with taxes and fees
The Budd-Pafford House - The Exploration Suite
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
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."
United States
C B.
$299 nightly
The price is $326
Oct 20 - Oct 21
Total with taxes and fees
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
Terrace/patio
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
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."
United States
Jenny K.
$306 nightly
The price is $354
Oct 20 - Oct 21
Total with taxes and fees
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
Exterior detail
SOUTHERN CHARM (Kid’s Bunk Room!)
SOUTHERN CHARM (Kid’s Bunk Room!)
10.0 out of 10, Exceptional, (73)
"Property was very clean and cool! "
United States
Carlyn B.
$302 nightly
The price is $349
Oct 20 - Oct 21
Total with taxes and fees
SOUTHERN CHARM (Kid’s Bunk Room!)
2 bedrooms, iron/ironing board, WiFi, bed sheets
Treehouse views in Historic Downtown Thomasville, Georgia
Treehouse views in Historic Downtown Thomasville, Georgia
$308 nightly
The price is $356
Oct 20 - Oct 21
Total with taxes and fees
Treehouse views in Historic Downtown Thomasville, Georgia
Fridge, microwave, oven, stovetop
Newly Built, Stunning 4BR/2BA with Waterfront Views
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. "
United States
RYAN H.
$362 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Boston vacation 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 low season months. For more hustle and bustle, you may prefer to visit Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston vacation 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 vacation.

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 vacation rentals in Boston?

Yes, you can find vacation rentals near well known attractions in Boston, or you can go with a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Boston?

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks: This vacation home rental near Boston offers a patio, a selection of games, and a barbecue grill 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 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 larger area, you’ll find Thomasville's Historic Big Oak and Pebble Hill Plantation.

What’s a vacation rental in Boston like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Boston. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip.