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Wellesley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (1,306 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is ￥21,172
￥23,649 total
includes taxes & fees
Nov 7 - Nov 8
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, (331 reviews)
"Area is quiet, building is modern, super clean and roomy. Plenty of places to eat within walking distance. Green line is an easy, short walk. Elevator wasn't working, but we were notified ahead of time and we easily managed the one flight of stairs. Would stay here again."
United States
Katerina
The price is ￥21,888
￥38,583 total
includes taxes & fees
Oct 14 - Oct 15
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 ￥21,804
￥35,827 total
includes taxes & fees
Nov 2 - Nov 3
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

4. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (362 reviews)
"Great spot, Clean, quiet, and convenient. Perfect no frills, no hassle spot in Boston. And very reasonably priced these days!"
United States
Ed
The price is ￥16,328
￥26,952 total
includes taxes & fees
Nov 2 - Nov 3
Premier Suites - Bay Village
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

5. 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 ￥21,172
￥35,650 total
includes taxes & fees
Oct 26 - Oct 27
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

6. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (498 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is ￥15,784
￥28,133 total
includes taxes & fees
Nov 3 - Nov 4
Temple Place Suites
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

7. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (155 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is ￥18,364
￥35,655 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 40 Temple St
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

8. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (436 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is ￥21,188
￥39,793 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A bedroom with a large bed, a smaller bed, a nightstand with a lamp, a mirror, and a window with a view of greenery.

9. Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston

Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
Watertown
9.8 out of 10, Exceptional, (65 reviews)
"I was very satisfied with my stay at this property. Mehmet, our host, made sure that we had everything we needed to make our stay comfortable. If I returned to this area, I would definitely stay here again."
United States
Melissa F.
The price is ￥20,382
￥35,650 total
includes taxes & fees
Oct 14 - Oct 15
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

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

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (94 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 ￥15,642
￥51,401 total
includes taxes & fees
Oct 18 - Oct 19
🎖The Boiler Room - Close to Subway & Downtown🎖
A brick building with a black front door, a staircase, and a well-maintained garden.

11. Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (37 reviews)
"Friendly hosts"
United States
Jan
The price is ￥15,010
￥34,261 total
includes taxes & fees
Oct 14 - Oct 15
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (28 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is ￥35,434
￥60,731 total
includes taxes & fees
Oct 28 - Oct 29
The Concord Hotel
A hallway with brick walls and a polished floor, leading to a door.

13. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (28 reviews)
"The place was great, and the host was even better! Very good communication and great customer service. I would highly recommend!"
United States
Travis
The price is ￥20,540
￥38,653 total
includes taxes & fees
Nov 2 - Nov 3
Enjoyable 2-bedroom lower level apartment in charming Lynn
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

14. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (19 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
The price is ￥14,710
￥39,028 total
includes taxes & fees
Nov 4 - Nov 5
Stunning Back Bay Studio Apartment
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

15. Modern Studio | South End

Modern Studio | South End
Back Bay
"The location was PERFECT! Very walkable, safe and close to the subway. Exceptional communication! We will chose to stay here again when in Boston."
United States
Lori
The price is ￥14,560
￥36,440 total
includes taxes & fees
Nov 1 - Nov 2
Modern Studio | South End
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

16. Stellar South End Studio

Stellar South End Studio
Back Bay
9.2 out of 10, Wonderful, (5 reviews)
"This place is not fancy, but is clean and comfortable and exactly as advertised I had an issue with the WiFi and the host fixed it as soon as they could. I would definitely stay here again."
United States
Daniel
The price is ￥19,592
￥45,150 total
includes taxes & fees
Oct 12 - Oct 13
Stellar South End Studio
A bedroom with a bed, a chair, a desk, a radiator, and a ceiling fan.

17. Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.6 out of 10, Excellent, (16 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
The price is ￥19,276
￥50,680 total
includes taxes & fees
Oct 12 - Oct 13
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
A modern hotel room with a bed, a desk, a sofa, and a dining area.

18. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (240 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is ￥35,234
￥67,746 total
includes taxes & fees
Oct 13 - Oct 14
Charlesgate Suites
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

19. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (325 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
The price is ￥28,440
￥49,037 total
includes taxes & fees
Nov 2 - Nov 3
Kasa Boston at Fenway
A residential house with a covered porch, a garage, and a well-maintained garden.

20. 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, (16 reviews)
"Will not be disappointed!"
United States
Dave O.
The price is ￥23,700
￥44,828 total
includes taxes & fees
Nov 2 - Nov 3
Charming 1-bedroom well located Garden Apartment in Historic West Medford
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

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

8/10 Good
"Very helpful and friendly staff"
Gordon 3-night trip
Posted less than an hour ago
Wyndham Boston Beacon Hill

Find out more about Wellesley

Search for holiday rentals in Wellesley on Expedia! You can easily find your home rentals, villas, holiday apartments in Wellesley using one of the methods below:

  • View our selection of featured holiday rentals in Wellesley
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Look no further and take a look at our great range of rental properties in Wellesley!

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.