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Wellesley Vacation Rentals

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Our top choices for Wellesley vacation rentals

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (105 reviews)
"host was so welcoming and we enjoyed they stay"
United States
Roshawn D.
$613 nightly
The price is $685
Jul 1 - Jul 2
Total with taxes and fees
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

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
$266 nightly
The price is $306
Jul 1 - Jul 2
Total with taxes and fees
Global Luxury Suites Downtown Boston

Bright 1 Bedroom | Downtown Boston

Bright 1 Bedroom | Downtown Boston
Bay Village
10.0 out of 10, Exceptional, (1 review)
"Great location to explore Boston with your dogs"
Canada
Thiery
$263 nightly
The price is $339
Jul 6 - Jul 7
Total with taxes and fees
Bright 1 Bedroom | Downtown Boston

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (393 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
$176 nightly
The price is $202
Jul 7 - Jul 8
Total with taxes and fees
Temple Place Suites

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
$174 nightly
The price is $200
Jun 21 - Jun 22
Total with taxes and fees
Maverick Suites at 40 Temple St

The Concord Hotel

The Concord Hotel
2.0 star property
South End
$271 nightly
The price is $311
Jun 21 - Jun 22
Total with taxes and fees
The Concord Hotel

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.
$238 nightly
The price is $280
Jun 21 - Jun 22
Total with taxes and fees
Studio Awaits Your Next Stay!

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
$192 nightly
The price is $220
Jun 21 - Jun 22
Total with taxes and fees
Maverick Suites at 245 Newbury St

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
$298 nightly
The price is $343
Jun 24 - Jun 25
Total with taxes and fees
Symple Live

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
$197 nightly
The price is $254
Jul 6 - Jul 7
Total with taxes and fees
Light-filled Studio | Back Bay

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (292 reviews)
"Great location and well maintained"
United States
EDDIE
$176 nightly
The price is $202
Jul 1 - Jul 2
Total with taxes and fees
Premier Suites - Bay Village

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (72 reviews)
"Excellent location, near grocery stores & public transport. Short walk to City Center (Copley Sq)."
United Kingdom
Jeremy
$194 nightly
The price is $223
Jun 21 - Jun 22
Total with taxes and fees
Maverick Suites at 402 Columbus Ave

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.
$355 nightly
The price is $408
Jul 15 - Jul 16
Total with taxes and fees
Primo North End Studio

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
$270 nightly
The price is $310
Jun 21 - Jun 22
Total with taxes and fees
The Chester Hotel

Downtown Studio | Students Welcome | W/D in unit

Downtown Studio | Students Welcome | W/D in unit
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Was worth the price all around"
United States
steven l.
$219 nightly
The price is $282
Jun 24 - Jun 25
Total with taxes and fees
Downtown Studio | Students Welcome | W/D in unit

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.6 out of 10, Exceptional, (10 reviews)
"Interesting space with great kitchen setup, roomy, private, and reasonably convenient, and host was responsive immediately when there were problems at check-in (broken lock box and open front door upon arrival). However: the floor was very much not clean (as in, our socks were dirty after ten minutes inside without shoes), the thermostat did not work, and there is a pet door to an outside hallway that cannot be shut/locked. (There's also a lot of noise from the facility upstairs during the day,...
United States
Anastasia P.
$246 nightly
The price is $270
Jul 6 - Jul 7
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (288 reviews)
"Amazing location we loved it"
United States
MARLYN
$323 nightly
The price is $371
Jun 21 - Jun 22
Total with taxes and fees
Kasa Boston at Fenway

Boston Financial District 1BR | Walk to anything!

Boston Financial District 1BR | Walk to anything!
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
$337 nightly
The price is $435
Jul 2 - Jul 3
Total with taxes and fees
Boston Financial District 1BR | Walk to anything!

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
$243 nightly
The price is $313
Jun 24 - Jun 25
Total with taxes and fees
Beautiful 1BR near Fenway Park + Kenmore!

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.8 out of 10, Excellent, (11 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
$389 nightly
The price is $418
Jul 1 - Jul 2
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wellesley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wellesley vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wellesley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $189 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wellesley rentals

At Expedia, we put the best Wellesley vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.