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Wellesley Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Wellesley vacation rentals

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,294 reviews)
"The full kitchen is amazing. The laundry soap provided was a nice surprise! It’s clean, quiet and gives a home like feeling for a hotel."
United States
Mrs. Andrea
The price is AED 592
AED 661 total
includes taxes & fees
4 Oct - 5 Oct
Crescent Suites Hotel
A wooden hallway with a patterned floor leading to a door.

2. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (323 reviews)
"Room was clean, neat area."
United States
Keir
The price is AED 449
AED 829 total
includes taxes & fees
30 Sep - 1 Oct
Maverick Suites at 89 Marion
A gazebo with a stone barbecue grill and a table with chairs.

3. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (70 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is AED 507
AED 833 total
includes taxes & fees
30 Sep - 1 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

4. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is AED 536
AED 1,270 total
includes taxes & fees
4 Oct - 5 Oct
Bright 2BR by Boston Waterfront
A living room with a sofa, a glass coffee table, a TV mounted on the wall, a wooden floor, and a window with a view of trees.

5. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (53 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
The price is AED 455
AED 796 total
includes taxes & fees
25 Oct - 26 Oct
NEW Modern Apartment Near Boston & Harvard Square.
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

6. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (352 reviews)
"Location is great"
United States
Eria
The price is AED 443
AED 699 total
includes taxes & fees
30 Sep - 1 Oct
Premier Suites - Bay Village
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is AED 606
AED 1,161 total
includes taxes & fees
30 Sep - 1 Oct
The Chester Hotel
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

8. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"A little issue getting in with the door code operation but otherwise great"
United States
Unspecified U.
The price is AED 356
AED 895 total
includes taxes & fees
4 Oct - 5 Oct
Sleek Studio Apartment in the South End
A stone house with a garden bed, a hose, and a brick pathway.

9. Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
The price is AED 529
AED 1,022 total
includes taxes & fees
5 Oct - 6 Oct
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

10. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (486 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is AED 463
AED 764 total
includes taxes & fees
29 Oct - 30 Oct
Temple Place Suites
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

11. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (92 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
The price is AED 367
AED 1,140 total
includes taxes & fees
18 Oct - 19 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

12. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is AED 544
AED 849 total
includes taxes & fees
26 Oct - 27 Oct
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A wooden front door with a glass panel and the number 383.

13. FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (52 reviews)
"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"
United States
Alicia R.
The price is AED 704
AED 1,488 total
includes taxes & fees
6 Oct - 7 Oct
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

14. Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
Quincy
9.6 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is AED 428
AED 1,151 total
includes taxes & fees
30 Sep - 1 Oct
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
A residential house with a covered porch, a garage, and a well-maintained garden.

15. Charming 1-bedroom well located Garden Apartment in Historic West Medford

Charming 1-bedroom well located Garden Apartment in Historic West Medford
West Medford
10.0 out of 10, Exceptional, (15 reviews)
"Will not be disappointed!"
United States
Dave O.
The price is AED 588
AED 1,047 total
includes taxes & fees
30 Sep - 1 Oct
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A modern kitchen with a large island, stainless steel appliances, and a minimalist design.

16. 3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C

3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
Ward Two
9.6 out of 10, Exceptional, (20 reviews)
"This place was great! Everything was very clean and new. It was easy to get in and out, and the host was extremely helpful and communicative. "
United States
Sierra K.
The price is AED 397
AED 1,354 total
includes taxes & fees
30 Sep - 1 Oct
3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
A modern kitchen with white cabinets, a central island, and a dining area set for six with white chairs and a marble table.

17. Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601

Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601
Mattapan
9.6 out of 10, Exceptional, (26 reviews)
"Was such a great spot for the 11 of us!! "
United States
Bryston J.
The price is AED 546
AED 1,485 total
includes taxes & fees
30 Sep - 1 Oct
Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

18. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (25 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is AED 677
AED 1,242 total
includes taxes & fees
30 Sep - 1 Oct
The Concord Hotel
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

19. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (175 reviews)
"Well located"
United States
Evelyn
The price is AED 536
AED 953 total
includes taxes & fees
30 Sep - 1 Oct
Maverick Suites at 400 Columbus Ave
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

20. Modern Studio | South End

Modern Studio | South End
Back Bay
The price is AED 448
AED 960 total
includes taxes & fees
19 Oct - 20 Oct
Modern Studio | South End
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.
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Top Wellesley Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Staff were helpful and super friendly! We traveled from Boston during the storm and they were able to check us in early which we truly appreciated. Room had an amazing ocean view and it was clean and was more than enough room for the 4 of us."
Rosario Cecilia 2-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

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 Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: This vacation home rental outside of Wellesley has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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.