Photo by Fun Travelog

Wellesley Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Wellesley

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (493)
"We enjoyed our stay. It was walkable to Chinatown. Very accessible to subway station. We liked that our room was on the top floor. "
The price is S$371
includes taxes & fees
26 Nov - 27 Nov
Global Luxury Suites Downtown Boston
Maverick Suites at 28 Fenway
3.0 star property
9.0 out of 10, Wonderful, (152)
"Everything good "
The price is S$294
includes taxes & fees
22 Dec - 23 Dec
Maverick Suites at 28 Fenway
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (951)
"This was my second time staying here. I love that the room is so clean and has a full kitchen. A nice quiet area of Waltham. "
The price is S$254
includes taxes & fees
2 Dec - 3 Dec
Crescent Suites Hotel
Temple Place Suites
2.5 star property
6.8 out of 10, (171)
"It was located conveniently for shops and the park and the rooms and bedding were very clean. The cleaning staff kept on top of the communal bathrooms but the cleanliness would depend on the guests that used it in between the cleaning. The picture you see in the advert is not the rooms i looked at or stayed in. The rooms are a lots more worn with some dark decor and peeling wallpaper with worn carpeting in areas, not polished wood floors as seen in pictures. That said it is clean, fresh clean...
The price is S$231
includes taxes & fees
15 Dec - 16 Dec
Temple Place Suites
Bay Village Suites
2.0 star property
6.4 out of 10, (135)
"It was cosy and worth the bucks "
Bay Village Suites
Sonder 907 Main
4.0 star property
8.2 out of 10, Very good, (403)
"Check in and out were both fast and easy thanks to the app. My only gripe is if you happen to be staying on the 4th floor like I did, be warned that there is a rooftop bar on the 5th floor so you’ll hear chairs pulling in and out until they close at midnight, followed by what I’m assuming is a garbage or mop bucket rolling around for a few hours after that. The patio from the adjoined restaurant Althea can get a little noisy as well, but it does die down around 10pm. "
The price is S$211
includes taxes & fees
21 Dec - 22 Dec
Sonder 907 Main
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (110)
"Fourth floor walk up, nice place. No front desk, all access information provided ahead of time. "
The price is S$352
includes taxes & fees
22 Dec - 23 Dec
Maverick Suites at 245 Newbury St
Maverick Suites at 89 Marion
2.0 star property
8.4 out of 10, Very good, (195)
"My flight arrived 4 hours earlier than planned, so I got to the hotel before the check-in time. One staff member noticed I was struggling and kindly offered to help. She checked if a room was available and let me check in an hour early. The service was excellent, the neighborhood was safe, and I thoroughly enjoyed my stay. I would highly recommend this hotel and would be happy to stay here again!"
The price is S$265
includes taxes & fees
24 Nov - 25 Nov
Maverick Suites at 89 Marion
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (849)
"Nice property, good sized and well furnished."
The price is S$234
includes taxes & fees
23 Dec - 24 Dec
No. 284 powered by Sonder
Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (132)
"Great location, great communication. Perfect place to stay if you just need a place to sleep close to the train station. Expect it to be… rustic. Bring shower shoes for the shared bathroom. The bed was super comfortable. It’s a tiny space, but has everything you need if you’re not going to be in the room much. Overall, good experience. Just don’t go into it expecting the space to be perfect."
Premier Suites - Bay Village
Maverick Suites at 40 Temple St
2.0 star property
7.4 out of 10, Good, (70)
"Beacon Hill is a good central location and about 30 minutes walk to the Convention Center. There’s a Whole Foods nearby for groceries. My room was small but fine for one person. Check in and out was easy. My only complaint was that there was no way to adjust the fan speed on the climate control and it was noidy but this was not a dealbreaker. "
The price is S$316
includes taxes & fees
22 Dec - 23 Dec
Maverick Suites at 40 Temple St
Global Luxury Suites East Boston
4.0 star property
7.0 out of 10, Good, (120)
"Good stay. No problems. Just need to work on communication before the stay and maybe get a 24 hr desk. Lovely apartment though and very clean. Lovely neighbourhood and right by the pier. Would love to come back "
The price is S$350
includes taxes & fees
25 Nov - 26 Nov
Global Luxury Suites East Boston
Sonder at Pierce Boston
4.0 star property
8.8 out of 10, Excellent, (207)
"Loved the views for this place! Its close to everything. There is no parking so we just ubered and walked everywhere. It was nice and clean"
The price is S$309
includes taxes & fees
19 Dec - 20 Dec
Sonder at Pierce Boston
Maverick Suites at 400 Columbus Ave
2.0 star property
7.6 out of 10, Good, (93)
"Having to have cleaning of the room as an extra charge should be noted clearly for any future occupants. The unit is not close to any restaurant or store unless you want to walk 10 minutes to get there and carry anything back. It is not convenient to anything of note. Would not stay there again. It was clean but that's the best I could say for the property. "
The price is S$294
includes taxes & fees
22 Dec - 23 Dec
Maverick Suites at 400 Columbus Ave
Maverick Suites at 402 Columbus Ave
2.5 star property
7.8 out of 10, Good, (49)
"Easy transaction and super convenient"
The price is S$294
includes taxes & fees
26 Nov - 27 Nov
Maverick Suites at 402 Columbus Ave
Sonder The Magnolia
3.5 star property
8.8 out of 10, Excellent, (49)
"This was in the heart of Back Bay. It was a cool experience to stay right on Newbury street. I had heard people complaining about noise but with some ear plugs it wasn’t a problem at all (they even supply a little white noise machine) but you are in the heart of the city you can’t be complaining about noise! The light in the bedroom was amazing. Our unit was the accessible unit so it had its own elevator! Quick walk to Copley station which is the perfect location on the Green Line cause you can...
The price is S$272
includes taxes & fees
8 Dec - 9 Dec
Sonder The Magnolia
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (166)
"Great space, great location. Just as advertised. Oct 2024 EVERYTHING looked new…floors, appliances, paint, furniture. Everything. Everything worked well ( though the fireplace would only stay lit for 5 minutes. Exactly FIVE). Communication was awesome. Prompt and helpful. Only criticism: did not know that there was NO ELEVATOR until the day of check in. At 61 with bad knees and four bags, getting settled in was a major hassle. Four narrow flights of winding stairs. Other than...
Charlesgate Suites
Sonder The Hancock
3.5 star property
7.8 out of 10, Good, (85)
"Nestled in the Government sector of town. Beautiful historical buildings and streets. Easy walk to most everywhere. "
The price is S$263
includes taxes & fees
12 Dec - 13 Dec
Sonder The Hancock
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.
Don't see what you're looking for?
See all available properties in Wellesley
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Wellesley you may be interested in

Seaport Hotel Boston
4.0 star property
9.6 out of 10, Exceptional, (2590)
"Amazing "
The price is S$258
includes taxes & fees
21 Dec - 22 Dec
Seaport Hotel Boston
Hilton Boston Park Plaza
4.0 star property
8.4 out of 10, Very good, (3285)
"I’ll start with the bad- laying in bed getting ready for bed and a mouse goes running across the floor. I notified front desk and was moved to another room. The good- the staff was friendly, the breakfast buffet was well stocked, and is centrally located to a lot of amenities. "
The price is S$253
includes taxes & fees
8 Dec - 9 Dec
Hilton Boston Park Plaza
Omni Parker House
4.0 star property
8.8 out of 10, Excellent, (2861)
"I couldn’t be more impressed with the level of service. From the moment I arrived the front desk staff went above and beyond to make me feel welcome. Check-in was smooth and efficient. Throughout my stay, the entire staff always responded and assisted promptly and kindly. "
The price is S$291
includes taxes & fees
30 Nov - 1 Dec
Omni Parker House
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.

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.