Wellesley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Wellesley vacation rentals

Rooftop terrace

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (631 reviews)
"Beautiful hotel and easy access to everything."
United States
Kimberely
The price is ￥48,482
￥55,730 total
includes taxes & fees
May 10 - May 11
Marriott Vacation Club® at Custom House, Boston
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (690 reviews)
"Great staff, clean, and location"
United States
Juan
The price is ￥26,371
￥37,321 total
includes taxes & fees
May 10 - May 11
Global Luxury Suites Downtown Boston
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (210 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is ￥33,106
￥65,110 total
includes taxes & fees
May 10 - May 11
Charlesgate Suites
Exterior

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (166 reviews)
"Great location. Well priced. Its appeals to a specific type of traveler. Overall clean, quiet, solid WiFi services. I had some initial challenges getting in the building, but that was my fault for not checking in and providing the required documents. I would definitely stay again. PS The pizza place right across the street makes a great thin crust pie. "
United States
James
The price is ￥22,653
￥40,416 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 245 Newbury St
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (112 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is ￥22,007
￥39,673 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 40 Temple St
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (274 reviews)
"Booked it for just 1 night. Attended a concert at the MGM 2 miles away. No street parking, its downtown Boston. We paid 38 bucks for overnight parking around the corner. Property was clean, but no heat, no hot water. March in Boston is freezing. The host answered fast w generic answers about heat n hot water."
United States
Wanya
The price is ￥16,804
￥27,432 total
includes taxes & fees
May 10 - May 11
Premier Suites - Bay Village
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (144 reviews)
"Great location!"
United States
Kevin
The price is ￥22,651
￥40,413 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 400 Columbus Ave
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (359 reviews)
"Great stay. "
United States
Anna
The price is ￥24,288
￥43,250 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 28 Fenway
Luxury Suite 3 | Living area | Smart TV, Netflix, Hulu, streaming services

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (36 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is ￥129,120
￥175,378 total
includes taxes & fees
May 25 - May 26
The Monty Boston
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very Good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is ￥25,983
￥49,708 total
includes taxes & fees
May 9 - May 10
The Chester Hotel
Apartment (1 Bedroom) | Interior

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is ￥25,793
￥64,481 total
includes taxes & fees
May 10 - May 11
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Apartment | 1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (14 reviews)
"Nice spot"
United States
Kimberly
The price is ￥28,870
￥49,772 total
includes taxes & fees
May 9 - May 10
Furnished Apartments near Encore Boston
Apartment, 2 Bedrooms | Interior

Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
9.0 out of 10, Wonderful, (11 reviews)
"Great property. Very clean and spacious. Easy 15 minutes walk to Harvard. Easy check in and check out process"
United States
Tho
The price is ￥43,289
￥67,795 total
includes taxes & fees
May 9 - May 10
Furnished Apts near Harvard Stadium
Exterior

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (71 reviews)
"Apartment has everything you need with a great location. Checkin was easy and rooms were very clean. "
United States
Clodagh
The price is ￥22,452
￥40,237 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 402 Columbus Ave
Interior entrance

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very Good, (283 reviews)
"Very nice and clean room, excellent location"
United States
Diana
The price is ￥21,417
￥37,892 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 89 Marion
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,186 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is ￥22,034
￥24,612 total
includes taxes & fees
Jun 7 - Jun 8
Crescent Suites Hotel
House | 5 bedrooms, desk

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is ￥45,945
￥110,983 total
includes taxes & fees
May 20 - May 21
Enchanting Hidden Door Escape
Indoor pool, pool umbrellas, sun loungers

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (188 reviews)
"Perfect location, professional staff, great parking arrangement "
United States
Joli
The price is ￥31,289
￥42,974 total
includes taxes & fees
May 24 - May 25
Global Luxury Suites East Boston
Interior

Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very Good, (237 reviews)
"Professional and courteous staff and i formative. Room was clean and well stocked with utensils and toiletries. Best olace ive been to so far. "
United States
Joan
The price is ￥16,804
￥18,770 total
includes taxes & fees
May 25 - May 26
Residences at Solomon Pond
House (3 Bedrooms) | Interior

Gillette Soccer Event HQ < 1 Mi to Patriot Place!

Gillette Soccer Event HQ < 1 Mi to Patriot Place!
3.0 star property
Foxborough
The price is ￥114,739
￥204,526 total
includes taxes & fees
May 11 - May 12
Gillette Soccer Event HQ < 1 Mi to Patriot Place!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wellesley Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Loved the location at the Seaport. The staff was helpful in choosing restaurants. They helped me get a great running trail. When it was raining the doorman was great and got me an umbrella before leaving. Breakfast was a good value and tasted good. Cleaning staff was courteous and did a great job. I would for sure come back!"
Patricia 3-night trip
Posted 6 hours ago
Seaport Hotel Boston

Find out more about Wellesley

Search for holiday rentals in Wellesley on Expedia! You can easily find your home rentals, villas, holiday apartments in Wellesley using one of the methods below:

  • View our selection of featured holiday rentals in Wellesley
  • Use the map to find apartments and other holiday homes in the Wellesley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wellesley while they last

Look no further and take a look at our great range of rental properties in Wellesley!

Frequently asked questions

Can I find vacation rentals in Wellesley?

Yes, there are vacation rentals in Wellesley close to Massachusetts Horticultural Society's Gardens at Elm Bank, or you can go with a more remote option if you're looking for extra privacy while you relax. Wellesley is known for its university setting and basketball games. Make sure you have time to check out the gardens while you're in the area.

What are some of the best vacation rentals that Wellesley has to offer?

Centrally located in the heart of Boston near T: This vacation home rental outside of Wellesley has air-conditioning and laundry facilities to help you feel perfectly comfortable 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.

How many vacation rentals are there in Wellesley?

Choose from 12 Expedia vacation rentals in Wellesley for a memorable vacation.

What can I see and do in Wellesley?

Charles River and Wellesley College Botanic Gardens are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Massachusetts Horticultural Society's Gardens at Elm Bank. Other popular places to visit in the area include Fenway Park and Gillette Stadium.

What are vacation rentals like in Wellesley?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Wellesley. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.