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Wellesley Vacation Rentals

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Vacation Rentals in Wellesley

"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
10.0 out of 10, Exceptional, (187)
"We really enjoyed our stay in Boston! Thanks for everything!"
The price is $375
$569 total
includes taxes & fees
May 21 - May 22
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
View from property
"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail
10.0 out of 10, Exceptional, (87)
"Great option for a unique stay in the Boston area with great access to downtown via a short, easy, inexpensive ferry ride."
The price is $475
$755 total
includes taxes & fees
May 20 - May 21
"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail
Pool
Beautiful Retreat close to Downtown Boston. Pets friendly.
9.8 out of 10, Exceptional, (81)
"Very clean, cute place. Area is a bit off main roads/hard to find food around - plan ahead"
The price is $126
$322 total
includes taxes & fees
May 21 - May 22
Beautiful Retreat close to Downtown Boston. Pets friendly.
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Interior
Boston's Finest New Renovated Apartment
9.8 out of 10, Exceptional, (21)
"Curtis’s place was perfect for my family and I visiting Boston, MA!"
Boston's Finest New Renovated Apartment
Dining
Fantastic 2 Bedroom Apartment Near Downtown
9.8 out of 10, Exceptional, (89)
"Very pleasant. Roomy, clean, well equipped. Neighborhood somewhat run down. On south side of city while tourist sites are on North side. We used Uber a lot. Overall nice stay. Thank you."
Fantastic 2 Bedroom Apartment Near Downtown
Marina
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
9.8 out of 10, Exceptional, (160)
"My son and I stayed here on a spring break trip. The location was a 5 min walk from the USS Constitution, a 10 min walk to Bunker Hill and a 20-30 min walk to the North End. However because we were on a boat in a marina there was zero traffic noise and that combined with the rocking motion of the houseboat meant I slept extremely well. Bonus: we were visited on several days by a pair of ducks who would hang out on the patio with us. Got to love a vacation home that comes with pets! Downsides?...
The price is $200
$567 total
includes taxes & fees
Jun 6 - Jun 7
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Interior
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
9.8 out of 10, Exceptional, (137)
"Great place! Was everything we needed and more"
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Deluxe Studio Suite | Living area
28 Fenway
2.0 star property
9.6 out of 10, Exceptional, (48)
"Cozy accommodations close to Back Bay and Fenway. A little too cozy for a couple - better for a solo leisure stay (no desk or working space). Rooms in pics look bigger than what it actually is. Garden level rooms will be a bit noisy. Excellent location and spotless and good security. "
28 Fenway
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (825)
"Our quick one night stay was great! Dana was very helpful at check in- a map of all the walkable restaurants for dinner and a recommendation for breakfast. The room was clean and the bed was comfortable. Would definitely stay here again."
The price is $179
$200 total
includes taxes & fees
May 27 - May 28
Crescent Suites Hotel
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (143)
"Great location, walking distance to Fenway. Very pleasant experience, would highly recommend."
Charlesgate Suites
Interior
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
9.6 out of 10, Exceptional, (124)
"It was everything we thought as far as location in the boat itself, but the exterior of the boat was in need of a cleaning the bathtowels. What didn't you and mildew smelling the betting was tingy. And a little smelly, but overall, the place was clean in general. And had everything you'd want or need."
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
Fridge, microwave, coffee/tea maker, toaster
Boston's Most Charming Bed & Breakfast - Heart of the City
9.6 out of 10, Exceptional, (97)
"Great property. Great location. Great owner and great / fast communicaton."
Boston's Most Charming Bed & Breakfast - Heart of the City
TV, DVD player, books, music library
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
9.6 out of 10, Exceptional, (132)
"Good location. Easy communications with host. Easy entrance and exit procedures."
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (777)
"Quiet at night yet just one block away from Newbury street with many restaurants, coffee shops and shopping."
The price is $288
$339 total
includes taxes & fees
May 27 - May 28
No. 284 powered by Sonder
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2203)
"Very clean and comfortable "
The price is $159
$178 total
includes taxes & fees
May 27 - May 28
HYATT house Boston/Burlington
Suite, 1 Double Bed, Accessible | 1 bedroom, individually decorated, individually furnished
Sonder The Magnolia
3.5 star property
9.0 out of 10, Wonderful, (32)
"The room/unit we were in was above shake shack so you could here the music and noise from the restaurant. Location was great for us though it was Midway between fenway and Boston common in back bay. We took the free logan express bus to back bay and the room was 1 block away. Only $3 to go back to the airport. "
The price is $439
$518 total
includes taxes & fees
May 27 - May 28
Sonder The Magnolia
Interior
90-Boston Spacious Convenient Apartment
9.0 out of 10, Wonderful, (24)
"We had a wonderful stay! The view from the kitchen window is amazing! Very convenient location. We were able to walk for groceries, dining and entertainment. Would definitely recommend. It was spacious and very cozy."
The price is $179
$417 total
includes taxes & fees
May 27 - May 28
90-Boston Spacious Convenient Apartment
Premier Apartment, 3 Bedrooms | Living area | 42-inch flat-screen TV with digital channels, TV, streaming services
Sonder at Pierce Boston
4.0 star property
8.8 out of 10, Excellent, (170)
"Very nice "
The price is $421
$496 total
includes taxes & fees
May 27 - May 28
Sonder at Pierce Boston
Interior
Sonder 907 Main
4.0 star property
8.2 out of 10, Very Good, (333)
"Fabulous location and the rooms are awesome. So Boston!!"
The price is $296
$343 total
includes taxes & fees
May 27 - May 28
Sonder 907 Main
Front of property
89 Marion
2.0 star property
8.2 out of 10, Very Good, (131)
"Good property in great walkable neighborhood. A little noise from the upstairs people on the floors but all manageable. Highly recommend."
The price is $176
$286 total
includes taxes & fees
May 27 - May 28
89 Marion
Don't see what you're looking for?
See all available properties in Wellesley
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.

Wellesley Vacation Rental Travel Info

Number of vacation rentals
13
Popular accommodation
Wellesley private vacation homes
Known landmarks
Legacy Place, Cochituate State Park and Larz Anderson Auto Museum
International airport
Boston, MA (BOS-Logan Intl.)

Other types of properties in Wellesley you may be interested in

Interior detail
The Dagny Boston
4.0 star property
9.2 out of 10, Wonderful, (3509)
"Dagny was a great stay. Reception staff were excellent and the rooms were fabulous, particularly the beds and bathroom. It can get a little noisy early in the morning with rubbish being emptied from the previous evening but, overall, it's a very good hotel"
The price is $206
$269 total
includes taxes & fees
May 27 - May 28
The Dagny Boston
Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2049)
"very clean property with a very helpful and professional staff."
The price is $197
$259 total
includes taxes & fees
Jun 9 - Jun 10
Omni Boston Hotel at the Seaport
Meeting facility
Hilton Boston Park Plaza
4.0 star property
8.4 out of 10, Very Good, (3320)
"Room was small and not well laid out. Bathroom was minuscule with no room to move. Closet had no light and no door, just flimsy curtain. No desk or work surface."
The price is $187
$259 total
includes taxes & fees
May 27 - May 28
Hilton Boston Park Plaza
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.

Everything you need to know about Wellesley 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 Wellesley 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 Wellesley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wellesley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wellesley. 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 Wellesley 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 $70 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 Wellesley rentals

At Expedia, we put the best Wellesley 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 Wellesley 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 Wellesley 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 Wellesley. 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

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?

Modern home-like 3BR2BA Retreat/Minutes to T: This vacation home rental outside of Wellesley is equipped with a balcony, 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.

How many vacation rentals are there in Wellesley?

Choose from 7 Expedia vacation rentals in Wellesley for a memorable vacation.

What can I see and do in Wellesley?

Elm Bank Reservation and Hemlock Gorge Reservation 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 TD Garden.

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.

Recent reviews of Wellesley properties
Expedia verified reviews

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

5/5 Excellent
"Amazing staff. Beautiful hotel"
A verified traveler stayed at Club Quarters Hotel Faneuil Hall, Boston
Posted 19 hours ago
Club Quarters Hotel Faneuil Hall, Boston