Boston Vacation Rentals

Start date: Check-in selected.
End date: Check-out

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Boston

Our top choices for Boston vacation rentals

Cottage On Park Ave. Off-season pricing.
Property grounds

Cottage On Park Ave. Off-season pricing.

10.0 out of 10, Exceptional, (182)
"Secluded and enjoyable. More comfortable than any hotel."
Cottage On Park Ave. Off-season pricing.
SOUTHERN CHARM (Kid’s Bunk Room!)
Exterior detail

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. "
$299 nightly
The price is $346
Sep 4 - Sep 5
Total with taxes and fees
SOUTHERN CHARM (Kid’s Bunk Room!)
Camellia Cottage - wheelchair friendly
Interior

Camellia Cottage - wheelchair friendly

10.0 out of 10, Exceptional, (4)
"Great, great place! I highly recommend when you are in the area!"
$177 nightly
The price is $193
Sep 29 - Sep 30
Total with taxes and fees
Camellia Cottage - wheelchair friendly
The Mash Manor
Exterior

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."
$535 nightly
The price is $617
Sep 4 - Sep 5
Total with taxes and fees
The Mash Manor
The Roost - Downtown Thomasville
Interior

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."
$271 nightly
The price is $279
Sep 22 - Sep 23
Total with taxes and fees
The Roost - Downtown Thomasville
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
Exterior

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

$674 nightly
The price is $694
Sep 7 - Sep 8
Total with taxes and fees
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
Charming 1-bedroom house in Metcalfe with modern amenities and a vintage vibe
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (8)
"Excellent stay!"
$149 nightly
The price is $175
Sep 14 - Sep 15
Total with taxes and fees
Charming 1-bedroom house in Metcalfe with modern amenities and a vintage vibe
Secluded pool home on 4+ acres
Terrace/patio

Secluded pool home on 4+ acres

10.0 out of 10, Exceptional, (23)
"This house suited our needs in preparing for a wedding and accommodating up to 10 people. Host is pleasant and easy to communicate with. Lovely pool and surrounds in which to relax. Monticello is a charming town as well."
Secluded pool home on 4+ acres
Newly Updated-Sprawling Ranch on Wimbledon
Fridge, microwave, oven, stovetop

Newly Updated-Sprawling Ranch on Wimbledon

2.0 star property
9.4 out of 10, Exceptional, (8)
"This was the perfect spot for our group of 6 attending a wedding in Thomasville. So close to everything and very spacious! We were even able to enjoy the backyard fire pit when a little cool front rolled in. "
$338 nightly
The price is $347
Sep 7 - Sep 8
Total with taxes and fees
Newly Updated-Sprawling Ranch on Wimbledon
Victoria's Secret Cottage (Downtown Thomasville) New Contrusction
Exterior detail

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

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!
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
TV, books

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. "
$299 nightly
The price is $306
Sep 7 - Sep 8
Total with taxes and fees
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Newly Built, Stunning 4BR/2BA with Waterfront Views
Fridge, microwave, oven, stovetop

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. "
$377 nightly
The price is $386
Sep 9 - Sep 10
Total with taxes and fees
Newly Built, Stunning 4BR/2BA with Waterfront Views
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (12)
"One of the best vacation rentals I have ever had the pleasure of renting."
$299 nightly
The price is $326
Sep 4 - Sep 5
Total with taxes and fees
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Fridge, microwave, oven, stovetop

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. "
$364 nightly
The price is $421
Sep 8 - Sep 9
Total with taxes and fees
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Georgia Blue Cottage
Outdoor dining

Georgia Blue Cottage

9.2 out of 10, Wonderful, (13)
"Great for 6 adults."
Georgia Blue Cottage
Mimosa Getaway - Less than 1 mile from Downtown
Fridge, microwave, oven, stovetop

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"
$316 nightly
The price is $323
Sep 7 - Sep 8
Total with taxes and fees
Mimosa Getaway - Less than 1 mile from Downtown
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Fridge, microwave, oven, stovetop

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"
$338 nightly
The price is $359
Sep 7 - Sep 8
Total with taxes and fees
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Hoodwood bed and breakfast
Fridge, microwave, oven, stovetop

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
Home Sweet Home
Outdoor dining

Home Sweet Home

10.0 out of 10, Exceptional, (15)
"The property was convenient."
Home Sweet Home
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Boston Hotel Reviews

Find out more about Boston

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 $175 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

SOUTHERN CHARM (Kid’s Bunk Room!): This vacation home rental near Boston is located in the city center 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.