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Top Holiday Rentals in Wellesley

"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
10.0 out of 10, Exceptional, (186)
"What an ideal spot for peace and solitude while in the heart of Boston! You are rocked to sleep on the water at night, with Boston attractions and history at your feet the next day. GT is super clean, well-appointed and almost as charming as its host Jon who is the best! Thank you and Karen for the goodies and a great stay. We’ll be back. Sara E. and Terrie S."
The price is £458
per night
11 May - 12 May
"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, (85)
"Stayed during the Boston marathon. The host was friendly and provided a lot of information about getting around town, things to do and places to eat."
The price is £610
per night
20 May - 21 May
"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, (80)
"Very clean, cute place. Area is a bit off main roads/hard to find food around - plan ahead"
The price is £270
per night
21 May - 22 May
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, (88)
"We loved our stay. The location was great the suite was amazing and was a great place to come home to after an amazing day in Boston. Thank you so much."
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 £430
per night
7 May - 8 May
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Deluxe Studio Suite | Living area
28 Fenway
2.0 star property
9.6 out of 10, Exceptional, (41)
"Great Location & I personally enjoy the fact that is a private residence. 👍 "
28 Fenway
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (821)
"I had a lovely suite overlooking the woods and the Charles River, where there is a lovely path for walking. I was surprised when I was told there was a full kitchen in the room, and discovered a living room, as well. I was only there for a night, but that would be a big perk if I was staying longer. The room and bathroom were clean. "
The price is £159
per night
5 May - 6 May
Crescent Suites Hotel
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (142)
"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, (131)
"I selected Gary’s property primarily because of the proximity of the Boston Convention center (We were able to walk there in about 15 minutes!), but the access to everything in downtown Boston was also fantastic. We were able to catch an Uber to anywhere we wanted to go in no more than 30 minutes. One small side note, there are 5 wall hanging artworks within the home that feature nude women; those with children or otherwise sensitive may wish to know."
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, (774)
"Quiet at night yet just one block away from Newbury street with many restaurants, coffee shops and shopping."
The price is £233
per night
27 May - 28 May
No. 284 powered by Sonder
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2195)
"Everything was good"
The price is £136
per night
10 May - 11 May
HYATT house Boston/Burlington
Comfort Suite, Kitchenette
Sonder The Magnolia
3.5 star property
9.2 out of 10, Wonderful, (31)
"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 £427
per night
7 May - 8 May
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 £337
per night
9 May - 10 May
90-Boston Spacious Convenient Apartment
Apartment, 2 Bedrooms | Living area | Flat-screen TV, streaming services
Sonder at Pierce Boston
4.0 star property
8.8 out of 10, Excellent, (169)
"Very nice "
The price is £419
per night
7 May - 8 May
Sonder at Pierce Boston
Fridge, microwave, oven, stovetop
233/3 Cozy modern apartment, Boston
8.4 out of 10, Very good, (6)
"Very convenient to where I needed to go during my trip to Boston."
The price is £347
per night
15 May - 16 May
233/3 Cozy modern apartment, Boston
Interior
Sonder 907 Main
4.0 star property
8.2 out of 10, Very good, (330)
"Great little hotel in beautiful and vibrant Cambridge area. Great restaurants and breakfast places around and if you like to walk like we do, not so bad to downtown. Room was beautifully designed and bed soo comfortable. Hotel doesn’t provide cleaning every day but not a problem for us. Will stay here if I’m Boston again."
The price is £268
per night
26 May - 27 May
Sonder 907 Main
Front of property
89 Marion
2.0 star property
8.2 out of 10, Very good, (130)
"Good property in great walkable neighborhood. A little noise from the upstairs people on the floors but all manageable. Highly recommend."
The price is £194
per night
6 May - 7 May
89 Marion
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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 Holiday Rental Travel Info

Number of holiday rentals
13
Popular accommodation
Wellesley private holiday 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

Everything you need to know about Wellesley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wellesley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wellesley holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wellesley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wellesley holiday rentals we have selected for you start as low as £136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wellesley rentals

At Expedia, we put the best Wellesley holiday 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 holiday.

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 holiday rentals in Wellesley?

Yes, there are holiday rentals in Wellesley close to Massachusetts Horticultural Society's Gardens at Elm Bank, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Wellesley has to offer?

Modern home-like 3BR2BA Retreat/Minutes to T: This holiday 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 that you can cook with friends or family.

How many holiday rentals are there in Wellesley?

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

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 holiday rentals like in Wellesley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wellesley. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.

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