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Wellesley Holiday Rentals

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Holiday Rentals in Wellesley

Lobby lounge
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (411)
"Decent place"
The price is NZ$540
includes taxes & fees
27 May - 28 May
Global Luxury Suites Downtown Boston
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2205)
"Very clean and comfortable "
The price is NZ$295
includes taxes & fees
6 Jun - 7 Jun
HYATT house Boston/Burlington
Deluxe Studio
Temple Place Suites
2.5 star property
6.8 out of 10, (83)
"Easily understood instructions for access to building and room. Great location. Bathrooms were not always clean. No windows in room. Good value for price"
The price is NZ$314
includes taxes & fees
9 Jun - 10 Jun
Temple Place Suites
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Deluxe Studio Suite | Living area
28 Fenway
2.0 star property
9.4 out of 10, Exceptional, (51)
"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, (831)
"The hotel was very nice but disappointed considering the price that there were not services, ie breakfast and round the clock manager on site."
The price is NZ$328
includes taxes & fees
27 May - 28 May
Crescent Suites Hotel
Interior
Sonder 907 Main
4.0 star property
8.2 out of 10, Very good, (337)
"Fabulous location and the rooms are awesome. So Boston!!"
The price is NZ$464
includes taxes & fees
16 Jun - 17 Jun
Sonder 907 Main
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
2.0 star property
6.0 out of 10, (58)
"For the price, this little gem of a room was perfect for my daughter and I wanting to just spend a few days exploring Boston on foot. "
Bay Village Suites
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (779)
"I used No 284 powered by Sonder as I was attending a conference in the Hynes conference center this week. The location is perfect and very close to the conference center and prudential shopping center, with plenty of great food and drink options close by. The room was spotless and very convenient with touchless check in and entry via an app. For the cost of the room, I would have expected a bit more space, but it is prime real estate in central Boston... All in all, great experience, would go...
The price is NZ$428
includes taxes & fees
17 Jun - 18 Jun
No. 284 powered by Sonder
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
2.0 star property
6.0 out of 10, (81)
"I recently stayed at a hotel in Boston with a bay view. The location of the hotel was great, and it was easy to communicate with the staff. However, I found that the building and room were starting to look tired and could use some updating. On the positive side, there were plenty of things to do in the area, and the check-in process was smooth. Overall, the hotel's location and communication were excellent, but improvements could be made in terms of the building and room condition."
Premier Suites - Bay Village
Rooftop terrace
Global Luxury Suites East Boston
4.0 star property
7.0 out of 10, Good, (87)
"Buy the parking in advance if you need it. They offer earlier check-in for a price too. Extremely beautiful area. Lost my key, luckily someone works there until 12am and Avis from customer service and Brandon at the front were amazing and helped us get back in our room after a concert. Worth the stay, just follow-up with what you need. "
The price is NZ$610
includes taxes & fees
27 May - 28 May
Global Luxury Suites East Boston
Front of property
89 Marion
2.0 star property
8.2 out of 10, Very good, (133)
"very lovely and high end classy stay with direct access to transportation and walkable to rests and trade joes'. however disappointingly lacked body bath soap!"
The price is NZ$377
includes taxes & fees
26 May - 27 May
89 Marion
Iron/ironing board, free WiFi
400 Columbus Avenue
2.0 star property
7.6 out of 10, Good, (56)
"It was not expensive and was perfect for someone who didn't spend much time in the room. Bed very comfortable."
The price is NZ$410
includes taxes & fees
26 May - 27 May
400 Columbus Avenue
Exterior
245 Newbury St
2.0 star property
8.0 out of 10, Very good, (79)
"Great location, no frill accommodations but it has all the basics. We come to Boston regularly, and you aren’t going to find a better location. If you are looking for an upscale place to stay, this isn’t it. But if you are looking for a clean, nice place with a great location, this is it. "
The price is NZ$467
includes taxes & fees
26 May - 27 May
245 Newbury St
Front of property
40 Temple St
2.0 star property
7.8 out of 10, Good, (55)
"Excellent stay in a convenient part of town. Love that everything was online and easy from booking, to checkin, property entry codes to checkout. Will stay again!"
The price is NZ$467
includes taxes & fees
25 May - 26 May
40 Temple St
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, (171)
"The Pierce was awesome! Beautiful views from the room, great location to go see a Sox game, super clean and great staff!!! I can’t say enough good things about it, if I go back to Boston, this is where I’m staying no question. "
The price is NZ$596
includes taxes & fees
23 Jun - 24 Jun
Sonder at Pierce Boston
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
Pool
Beautiful Retreat close to Downtown Boston. Pets friendly.
9.8 out of 10, Exceptional, (82)
"We came for my graduation and everything was awesome. Driving to the inner city can be chaotic. This was just close enough where we could enjoy the piece and quiet at the end of the day, while still being close to where wr needed to be. Everything was clean and beautiful. If you have the opportunity to stay here, do it. You will not regret it."
The price is NZ$523
includes taxes & fees
4 Jun - 5 Jun
Beautiful Retreat close to Downtown Boston. Pets friendly.
Apartment
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
Suite, 1 Double Bed, Accessible
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 NZ$692
includes taxes & fees
17 Jun - 18 Jun
Sonder The Magnolia
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
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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.

Other types of properties in Wellesley you may be interested in

Exterior
Seaport Hotel Boston
4.0 star property
9.6 out of 10, Exceptional, (2157)
"All of the employees of the hotel were so wonderful and helpful, which made our stay at the hotel so great."
The price is NZ$573
includes taxes & fees
6 Jun - 7 Jun
Seaport Hotel Boston
Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2072)
"great property convenient location. I would say again "
The price is NZ$381
includes taxes & fees
27 May - 28 May
Omni Boston Hotel at the Seaport
Meeting facility
Hilton Boston Park Plaza
4.0 star property
8.4 out of 10, Very good, (3325)
"Great location. Beautiful interior. Coffee and dining on site. Clean rooms."
The price is NZ$422
includes taxes & fees
26 May - 27 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wellesley holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wellesley. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wellesley. Seeing all the best attractions is bound to make you fall in love with Wellesley. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wellesley short-term rentals, that won’t be hard to do.

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.

Recent reviews of Wellesley properties
Expedia verified reviews