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Wellesley Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Wellesley vacation rentals

Terrace/patio

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,262 reviews)
"Friendly staff. Bed was very comfortable and the kitchen was a plus!"
United States
Evelyn
$157 nightly
The price is $175
Sep 6 - Sep 7
Total with taxes and fees
Crescent Suites Hotel
Deluxe Double Room, Shared Bathroom

2. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (333 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
$154 nightly
The price is $177
Sep 1 - Sep 2
Total with taxes and fees
Premier Suites - Bay Village
Lobby

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (309 reviews)
"Amazing location we loved it"
United States
MARLYN
$296 nightly
The price is $340
Sep 7 - Sep 8
Total with taxes and fees
Kasa Boston at Fenway
Rooftop terrace

4. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (661 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
$390 nightly
The price is $448
Sep 2 - Sep 3
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)

5. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (452 reviews)
"Great location so close to everything"
United States
Hunter
$163 nightly
The price is $187
Aug 31 - Sep 1
Total with taxes and fees
Temple Place Suites
Front of property

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (411 reviews)
"Good clear communication. Great location! Walked to Fenway for a game. All kinds of restaurants close. Nice clean, comfortable room in a beautifully maintained building!"
United States
James
$298 nightly
The price is $342
Sep 6 - Sep 7
Total with taxes and fees
Maverick Suites at 28 Fenway
Exterior

7. 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)
"Great location, really cool place!"
United States
lane
$246 nightly
The price is $283
Aug 31 - Sep 1
Total with taxes and fees
Maverick Suites at 245 Newbury St
Living area

8. 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
$244 nightly
The price is $280
Aug 31 - Sep 1
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Room

9. Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Fenway–Kenmore
9.8 out of 10, Exceptional, (9 reviews)
"Great location with comfortable accommodations!! Easy access to great restaurants, Fenway, and the T. Host provided excellent communication and was extremely responsive. Highly recommend!"
United States
Andrea G.
$283 nightly
The price is $333
Sep 9 - Sep 10
Total with taxes and fees
Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Premium Studio Suite

10. 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
$328 nightly
The price is $377
Sep 7 - Sep 8
Total with taxes and fees
Charlesgate Suites
Interior entrance

11. 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
$282 nightly
The price is $315
Sep 6 - Sep 7
Total with taxes and fees
Maverick Suites at 89 Marion
Studio

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.8 out of 10, Good, (19 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
$294 nightly
The price is $338
Sep 9 - Sep 10
Total with taxes and fees
The Concord Hotel
Front of property

13. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (143 reviews)
"Worth the stay"
Canada
Akansha
$244 nightly
The price is $280
Aug 31 - Sep 1
Total with taxes and fees
Maverick Suites at 40 Temple St
Living area

14. Wonderful Fenway 3br/2ba | Steps from Fenway Park!

Wonderful Fenway 3br/2ba | Steps from Fenway Park!
Fenway–Kenmore
10.0 out of 10, Exceptional, (4 reviews)
"Strong location and good spaces"
United States
Bryce G.
$470 nightly
The price is $552
Sep 7 - Sep 8
Total with taxes and fees
Wonderful Fenway 3br/2ba | Steps from Fenway Park!
Exterior

15. Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
9.0 out of 10, Wonderful, (15 reviews)
"The communication with the host was very easy. Great location!"
Canada
Josee
$277 nightly
The price is $298
Aug 31 - Sep 1
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
Lobby lounge

16. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (738 reviews)
"Great for the price; central to everything"
United States
afshin
$294 nightly
The price is $337
Sep 7 - Sep 8
Total with taxes and fees
Global Luxury Suites Downtown Boston
Room

17. Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.6 out of 10, Excellent, (8 reviews)
"Would stay again"
United States
mark p.
$221 nightly
The price is $260
Aug 31 - Sep 1
Total with taxes and fees
Studio Awaits Your Next Stay!
Luxury Suite 3 | Living area

18. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
$757 nightly
The price is $870
Aug 31 - Sep 1
Total with taxes and fees
The Monty Boston
Suite (Luxury 1BR w/ King Bed & City Views)

19. 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
$370 nightly
The price is $426
Sep 14 - Sep 15
Total with taxes and fees
Symple Live
Exterior

20. 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.
$255 nightly
The price is $300
Sep 3 - Sep 4
Total with taxes and fees
Sleek Studio Apartment in the 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 Dagny Boston

The Dagny Boston

10/10 Excellent
"The Dagny was amazing, we dropped our bags off at concierge to John at 7am. He was great as well as the bellman Eddie, they really made you feel welcomed & at home. We were lucky enough to have got an early check in at 10am!! So we didn’t have to wait around until 4pm. Room was super spacious & clean. You’re in walking distance of everything, maybe 25-30 min. walk to local staples. Super safe stay in the Financial District. Definitely recommend staying here!!"
Nickolas 3-night trip
Posted 6 hours ago
The Dagny Boston

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 $175 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 TD Garden.

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.