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Wellesley Vacation Rentals

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Our top choices for Wellesley vacation rentals

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (396 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is CA $166
CA $280 total
includes taxes & fees
Jun 27 - Jun 28
Temple Place Suites

The Concord Hotel

The Concord Hotel
2.0 star property
South End
The price is CA $250
CA $467 total
includes taxes & fees
Jun 30 - Jul 1
The Concord Hotel

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is CA $226
CA $439 total
includes taxes & fees
Jun 30 - Jul 1
The Chester Hotel

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (294 reviews)
"Great location and well maintained"
United States
EDDIE
The price is CA $171
CA $269 total
includes taxes & fees
Jun 30 - Jul 1
Premier Suites - Bay Village

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
The price is CA $113
CA $352 total
includes taxes & fees
Jul 6 - Jul 7
Light-filled Studio | Back Bay

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (376 reviews)
"Great stay. "
United States
Anna
The price is CA $185
CA $351 total
includes taxes & fees
Jun 28 - Jun 29
Maverick Suites at 28 Fenway

Simple Theater District 1 Bedroom

Simple Theater District 1 Bedroom
Bay Village
8.0 out of 10, Very good, (2 reviews)
"It was clean and in a convenient location, and mostly had what we needed for our stay - basically a place to leave our stuff during the day and a place to sleep at night. There is no place in the bedroom for clothes except the closet; no shelves, no dresser, not even a folding luggage rack - though there is a giant full-length mirror. In the bathroom, there are only two small wire hooks for towels and no place except the back of the toilet and along the sink to put one's toiletries. There isn't...
United States
Sue F.
The price is CA $167
CA $476 total
includes taxes & fees
Jun 30 - Jul 1
Simple Theater District 1 Bedroom

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (156 reviews)
"Great location!"
United States
Kevin
The price is CA $233
CA $268 total
includes taxes & fees
Jun 30 - Jul 1
Maverick Suites at 400 Columbus Ave

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (707 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is CA $254
CA $454 total
includes taxes & fees
Jul 7 - Jul 8
Global Luxury Suites Downtown Boston

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very good, (23 reviews)
"Friendly hosts"
United States
Jan
The price is CA $204
CA $400 total
includes taxes & fees
Jun 30 - Jul 1
Free Parking at 1 Bed Basement Apt, Near BU & MIT

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, (175 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is CA $271
CA $312 total
includes taxes & fees
Jun 24 - Jun 25
Maverick Suites at 245 Newbury St

Downtown Crossing, Affordable Stay, Book Now!

Downtown Crossing, Affordable Stay, Book Now!
Downtown Boston
6.2 out of 10, (14 reviews)
"Great location!"
United States
Sean
The price is CA $222
CA $407 total
includes taxes & fees
Jun 28 - Jun 29
Downtown Crossing, Affordable Stay, Book Now!

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport
Downtown Boston
9.6 out of 10, Exceptional, (4 reviews)
"Location was awesome and central to the attractions. "
United States
Shelly B.
The price is CA $304
CA $741 total
includes taxes & fees
Jul 14 - Jul 15
Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (4 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is CA $286
CA $467 total
includes taxes & fees
Jun 24 - Jun 25
Symple Live

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very good, (21 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
The price is CA $222
CA $409 total
includes taxes & fees
Jun 30 - Jul 1
Perfect One Bedroom Stay In Downtown Boston!

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (15 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is CA $283
CA $586 total
includes taxes & fees
Jul 15 - Jul 16
Primo North End Studio

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (121 reviews)
"This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
United States
Rachel
The price is CA $251
CA $288 total
includes taxes & fees
Jul 6 - Jul 7
Maverick Suites at 40 Temple St

North End Studio

North End Studio
North End
9.4 out of 10, Exceptional, (59 reviews)
"Yes, kitchen was fully stocked with all dishes, glasses, cookware, and silverware. Even had paper products and all cleaning items. Place was very clean!!!"
United States
Kimberly
The price is CA $283
CA $586 total
includes taxes & fees
Jun 24 - Jun 25
North End Studio

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.4 out of 10, Very good, (6 reviews)
"Would stay again"
United States
mark p.
The price is CA $215
CA $399 total
includes taxes & fees
Jun 27 - Jun 28
Studio Awaits Your Next Stay!

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (14 reviews)
"Perfect location, terrible cleanliness."
United States
Cristina
The price is CA $127
CA $399 total
includes taxes & fees
Jun 24 - Jun 25
Cozy Studio Steps from Boston Common and Theaters
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Boston's Best Vacation Home : This vacation 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 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.