Boston Vacation Rentals from $296: Search Short-Term Rentals

Q: 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.

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In two weeks

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Our top choices for Boston vacation rentals

2 bedrooms, iron/ironing board, travel crib, WiFi

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

Thomasville

Andrew K.

$254 nightly

May 10 - May 11

Total with taxes and fees

2 bedrooms, iron/ironing board, WiFi, bed sheets

Mimosa Cottage - Near Downtown Thomasville

Thomasville

Russ W.

$294 nightly

May 11 - May 12

Total with taxes and fees

An elegant waterside retreat in the Red Hills

Thomasville

brittiny c.

$292 nightly

May 11 - May 12

Total with taxes and fees

Camellia Cottage - wheelchair friendly

Monticello

Teresa

$218 nightly

May 18 - May 19

Total with taxes and fees

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

Monticello

ROBERT B.

$299 nightly

May 10 - May 11

Total with taxes and fees

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

Thomasville

Frederick E

$388 nightly

May 18 - May 19

Total with taxes and fees

Mimosa Getaway - Less than 1 mile from Downtown

Thomasville

Emily H.

$316 nightly

May 10 - May 11

Total with taxes and fees

The Budd-Pafford House - The Exploration Suite

Monticello

Jennifer T.

$226 nightly

May 10 - May 11

Total with taxes and fees

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Top Boston Hotel Reviews

Holiday Inn Express & Suites Thomasville by IHG

8/10 Good

"The staff was so friendly and welcoming. The rooms were clean and the hotel felt safe "

Baymont by Wyndham Thomasville

2/10 Terrible

"the hotel was dirty, had no soap, stained sheets, filthy curtains and grounds were were unkept. I had reservations for 2 nights but left after the first night due to condition of the room even though I was going to have to pay for the 2nd night. Was extremely dissapointed as I have always felt comfortable booking a "Wyndham" hotel but instead felt like we were not safe. The hotel staff did not have a professional appearance, they were sloppily dressed, had missing teeth and I would think Wyndham would expect a more professional look to represent their brand."

Red Roof Inn & Suites Thomasville

2/10 Terrible

"1st night we asked for an extra wash cloth and towel because there qas only 2 of each in the room, was told they didnt have any. We lefted the next morning to go back into Tallahassee, the reason for our trip. We got back to hotel about 8, dirty towels weren't removed. Husband went to get fresh ones. The lady at the counter stated she couldnt get any clean ones, that they were locked in laundry room and she didnt have a key. I was ok with, stuff happens, Husband was NOT happy. 10 minutes later we get a knock on the door asking which vehicle was ours, i told her and front desk lady said that tshe was told the "Marijuana" smell that was outside was going from our vehicle. I politely told her no, that it was there when we got back and that my husband was a Paramedic and could lose his licenses for that! Exterior doors were slammed the rest of the night into the morning. I went to check out and asked for receipt, no printer paper. "

Quality Inn & Suites Conference Center

2/10 Terrible

"This was an absolutely horrible experience from beginning to end. The staff was lazy and rude and that’s before I got into the room of horror. You could barely shut the bathroom door because it was so close to the shower and wall.. you had to step back and stand back over the toilet to shut the door and this was called a ^ mini sweet ^. The couch bed had stains on the matress and the sheets they included had stains all over them . My husband had to walk back down and around in the rain to get an attitude from the guy behind the counter to get new sheets. We had no choice but to stay there because we got there at 10:30 pm . We came up to the area as my daughter’s graduation from FSU the next day . We couldn’t shower because it looked like someone had showered there before we checked in . Any absolute disgusting and disgraceful place to stay ."

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 $296 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.

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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.

Boston Vacation Rentals

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Check prices for these dates

Our top choices for Boston vacation rentals

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

Mimosa Cottage - Near Downtown Thomasville

An elegant waterside retreat in the Red Hills

Camellia Cottage - wheelchair friendly

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

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

Mimosa Getaway - Less than 1 mile from Downtown

The Budd-Pafford House - The Exploration Suite

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

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

The Roost - Downtown Thomasville

Modern Home Near Downtown Thomasville

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

Sprawling Updated Ranch with Fireplace on Wimbledon

Treehouse views in Historic Downtown Thomasville, Georgia

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

Mimosa Stay Cottage - Thomasville Close to all the Charm

SOUTHERN CHARM (Kid’s Bunk Room!)

New!! Remodeled downtown home. Golf cart available to rent. Walk to Broad St.

Find vacation rentals that suit your style

Top Boston Hotel Reviews

Holiday Inn Express & Suites Thomasville by IHG

Find out more about Boston

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