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Boston Vacation Rentals

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Our top choices for Boston vacation rentals

Camellia Cottage - wheelchair friendly

Camellia Cottage - wheelchair friendly
Monticello
9.6 out of 10, Exceptional, (18 reviews)
"Great location, clean, and comfortable. "
United States
Teresa
$199 nightly
The price is $217
Jun 24 - Jun 25
Total with taxes and fees
Camellia Cottage - wheelchair friendly

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (60 reviews)
$292 nightly
The price is $312
Jun 21 - Jun 22
Total with taxes and fees
Newly Renovated - Thomasville Getaway - Large Fenced Backyard

An elegant waterside retreat in the Red Hills

An elegant waterside retreat in the Red Hills
Thomasville
9.8 out of 10, Exceptional, (31 reviews)
"Quiet, peaceful surroundings "
United States
Lili G.
$286 nightly
The price is $306
Jun 22 - Jun 23
Total with taxes and fees
An elegant waterside retreat in the Red Hills

Charming 2-bedroom cottage built with children and pets in mind.

Charming 2-bedroom cottage built with children and pets in mind.
Thomasville
9.6 out of 10, Exceptional, (10 reviews)
"Host was very responsive and accommodating. Home was comfortable and well equipped. Would book again!"
United States
Andrew K.
$244 nightly
The price is $283
Jun 18 - Jun 19
Total with taxes and fees
Charming 2-bedroom cottage built with children and pets in mind.

The Budd-Pafford House - The Exploration Suite

The Budd-Pafford House - The Exploration Suite
Monticello
9.0 out of 10, Wonderful, (13 reviews)
"Beautiful, clean home. Well stocked kitchen and bedroom/bathroom. My bed was wonderful. The house is within walking distance to many restaurants, shops, markets, etc. Wonderful location."
United States
Jennifer T.
$225 nightly
The price is $245
Jun 18 - Jun 19
Total with taxes and fees
The Budd-Pafford House - The Exploration Suite

The Budd-Pafford House: The Rose Room

The Budd-Pafford House: The Rose Room
Monticello
8.2 out of 10, Very Good, (10 reviews)
$195 nightly
The price is $213
Jun 18 - Jun 19
Total with taxes and fees
The Budd-Pafford House: The Rose Room

The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Excellent stay!"
United States
Becky A W.
$253 nightly
The price is $270
Jun 21 - Jun 22
Total with taxes and fees
The Roost - Downtown Thomasville

Mimosa Getaway - Less than 1 mile from Downtown

Mimosa Getaway - Less than 1 mile from Downtown
Thomasville
9.6 out of 10, Exceptional, (13 reviews)
"Great place, perfect for the weekend. "
United States
bill W.
$312 nightly
The price is $333
Jul 5 - Jul 6
Total with taxes and fees
Mimosa Getaway - Less than 1 mile from Downtown

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, (30 reviews)
$348 nightly
The price is $372
Jun 21 - Jun 22
Total with taxes and fees
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

QUAIL COTTAGE - Downtown Thomasville!

QUAIL COTTAGE - Downtown Thomasville!
Thomasville
10.0 out of 10, Exceptional, (141 reviews)
"Perfect place to stay, clean, close to everything, Would stay again and highly recommend!"
United States
Molly S.
$301 nightly
The price is $349
Jun 18 - Jun 19
Total with taxes and fees
QUAIL COTTAGE - Downtown Thomasville!

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, (23 reviews)
"Clean great location and very friendly thank you for the stay we will be back"
United States
ROBERT B.
$298 nightly
The price is $325
Jun 18 - Jun 19
Total with taxes and fees
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

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

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
9.8 out of 10, Exceptional, (17 reviews)
"The property was clean and spacious for our family. The access were very easy."
United States
Frederick E
$372 nightly
The price is $397
Jun 24 - Jun 25
Total with taxes and fees
Newly Built, Stunning 4BR/2BA with Waterfront Views

Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.6 out of 10, Exceptional, (20 reviews)
"Was a very comfortable home for our girl’s trip of 5 ladies! "
United States
Julia N.
$352 nightly
The price is $376
Jun 22 - Jun 23
Total with taxes and fees
Sprawling Updated Ranch with Fireplace on Wimbledon

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, (5 reviews)
"Great location spacious layout furnished perfectly "
United States
Damian Ray V.
$308 nightly
The price is $329
Jul 6 - Jul 7
Total with taxes and fees
Mimosa Stay Cottage - Thomasville Close to all the Charm

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

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Thomasville
9.6 out of 10, Exceptional, (10 reviews)
"Great place"
United States
Michael S.
$342 nightly
The price is $365
Jul 6 - Jul 7
Total with taxes and fees
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

Dog friendly nature preserve Monticello, FL

Dog friendly nature preserve Monticello, FL
Monticello
10.0 out of 10, Exceptional, (2 reviews)
"Nice rustic environment and very pet friendly."
United States
Jeff B.
$198 nightly
The price is $216
Jun 30 - Jul 1
Total with taxes and fees
Dog friendly nature preserve Monticello, FL

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, (19 reviews)
"Our stay was absolutely wonderful! Will definitely be booking here again!"
United States
Unspecified U.
$389 nightly
The price is $449
Jun 21 - Jun 22
Total with taxes and fees
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, (28 reviews)
"Perfect place for our group of 5! Everyone had their own bedroom and bath and the house was spacious and just beautiful! We loved the quick walk to downtown Thomasville and all the holiday festivities. The owner was very responsive and helpful as well. "
United States
Debra B.
$576 nightly
The price is $664
Jun 22 - Jun 23
Total with taxes and fees
The Mash Manor

Southern Charm Home: Pool + Fireplace + Large Yard

Southern Charm Home: Pool + Fireplace + Large Yard
Thomasville
10.0 out of 10, Exceptional, (3 reviews)
"Convenient location and has everything you need."
United States
Dee J.
$417 nightly
The price is $446
Jul 13 - Jul 14
Total with taxes and fees
Southern Charm Home: Pool + Fireplace + Large Yard

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, (11 reviews)
"Nicely equipped kitchen , great areas to relax and very quiet "
United States
Jesse V.
$614 nightly
The price is $658
Jun 30 - Jul 1
Total with taxes and fees
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
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 $306 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?

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!: This vacation home rental near Boston is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 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.