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Our top choices for Wellesley holiday rentals

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,257 reviews)
"The hotel was conveniently located with lots of good dining options nearby. The room was very clean, quiet and comfortable ."
United States
CHRISTINE
The price is £132
includes taxes & fees
20 Sept - 21 Sept
Crescent Suites Hotel

2. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (451 reviews)
"Great location so close to everything"
United States
Hunter
The price is £128
includes taxes & fees
27 Aug - 28 Aug
Temple Place Suites

3. 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, (8 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is £162
includes taxes & fees
6 Sept - 7 Sept
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

4. 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 £215
includes taxes & fees
3 Sept - 4 Sept
Sleek Studio Apartment in the South End

5. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (331 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
The price is £121
includes taxes & fees
27 Aug - 28 Aug
Premier Suites - Bay Village

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (410 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is £199
includes taxes & fees
27 Aug - 28 Aug
Maverick Suites at 28 Fenway

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (37 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is £285
includes taxes & fees
27 Aug - 28 Aug
The Chester Hotel

8. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (201 reviews)
The price is £193
includes taxes & fees
31 Aug - 1 Sept
Maverick Suites at 245 Newbury St

9. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (19 reviews)
"Great location to fenway. Easy and clean."
United States
Allison
The price is £316
includes taxes & fees
7 Sept - 8 Sept
Symple Live

10. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (17 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 £236
includes taxes & fees
27 Aug - 28 Aug
The Concord Hotel

11. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (142 reviews)
"Worth the stay"
Canada
Akansha
The price is £186
includes taxes & fees
30 Aug - 31 Aug
Maverick Suites at 40 Temple St

12. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.4 out of 10, Exceptional, (10 reviews)
"It was a great stay!"
United States
Adina S.
The price is £195
includes taxes & fees
30 Aug - 31 Aug
Light-filled Studio | Back Bay

13. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (168 reviews)
"Well located"
United States
Evelyn
The price is £192
includes taxes & fees
30 Aug - 31 Aug
Maverick Suites at 400 Columbus Ave

14. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (228 reviews)
"Kitchen is excellent and rooms excellent"
United States
AKIN
The price is £280
includes taxes & fees
7 Sept - 8 Sept
Charlesgate Suites

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (310 reviews)
"Stayed in the economy suite, very suitable for a couple! Very clean room and I have never had an easier check-in process!!"
United States
Paula
The price is £174
includes taxes & fees
27 Aug - 28 Aug
Maverick Suites at 89 Marion

16. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is £275
includes taxes & fees
20 Sept - 21 Sept
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

17. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (29 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is £264
includes taxes & fees
1 Sept - 2 Sept
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

18. Studio in the Heart of Boston!

Studio in the Heart of Boston!
Downtown Boston
10.0 out of 10, Exceptional, (3 reviews)
"My stay was excellent! One of the best parts was how responsive the property management team was to communicate with me so quickly on the VRBO app."
United States
Landon W.
The price is £215
includes taxes & fees
7 Sept - 8 Sept
Studio in the Heart of Boston!

19. 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, (67 reviews)
"Great stay! Highly recommend! "
United States
Valeria M.
The price is £172
includes taxes & fees
7 Sept - 8 Sept
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

20. Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.6 out of 10, Excellent, (8 reviews)
The price is £190
includes taxes & fees
30 Aug - 31 Aug
Studio Awaits Your Next Stay!
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

Find out more about Wellesley

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 £121 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?

Boston's Best Vacation Home : This holiday home rental outside of Wellesley is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

How many holiday rentals are there in Wellesley?

Choose from 12 Expedia holiday rentals in Wellesley for a memorable holiday.

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 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.