Wellesley Vacation Rentals

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Vacation Rentals in Wellesley

Exterior
Spacious Private Entrance Master Bedroom/Bath

Spacious Private Entrance Master Bedroom/Bath

Wellesley
10.0 out of 10, Exceptional, (89)
"Great place to stay. "
United States
Alexa
$157 nightly
The price is $172
Dec 18 - Dec 19
Total with taxes and fees
Spacious Private Entrance Master Bedroom/Bath
Interior
Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI

Boston
9.8 out of 10, Exceptional, (89)
"Such a unique experience.We loved the relaxing views after a long day of site seeing.Great access to sites and airport."
United States
Laura M.
$383 nightly
The price is $440
Dec 8 - Dec 9
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
Marina
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Charlestown
9.8 out of 10, Exceptional, (200)
"My husband and I had an excellent stay! It was very comfortable! I would highly recommend staying on The Blue Pearl and hope to stay there again. "
United States
Stacey W.
$405 nightly
The price is $466
Dec 8 - Dec 9
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Bay Village Suites

2.0 star property
Bay Village
6.4 out of 10, (249)
"Great location nice neighborhood "
United States
Jose
$145 nightly
The price is $167
Dec 8 - Dec 9
Total with taxes and fees
Bay Village Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Temple Place Suites

2.5 star property
Downtown Boston
7.0 out of 10, Good, (323)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
$155 nightly
The price is $178
Dec 8 - Dec 9
Total with taxes and fees
Temple Place Suites
Exterior
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, (154)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
$194 nightly
The price is $223
Jan 4 - Jan 5, 2026
Total with taxes and fees
Maverick Suites at 245 Newbury St
Lobby lounge
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4.0 star property
Chinatown
8.0 out of 10, Very Good, (628)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
$142 nightly
The price is $163
Dec 18 - Dec 19
Total with taxes and fees
Global Luxury Suites Downtown Boston
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Premier Suites - Bay Village

2.0 star property
Bay Village
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
$125 nightly
The price is $144
Dec 8 - Dec 9
Total with taxes and fees
Premier Suites - Bay Village
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2.0 star property
South End
7.2 out of 10, Good, (132)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
$172 nightly
The price is $198
Dec 17 - Dec 18
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
1 bedroom, desk, iron/ironing board, WiFi
Best Location Studio In Downtown Boston

Best Location Studio In Downtown Boston

Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
$185 nightly
The price is $217
Dec 11 - Dec 12
Total with taxes and fees
Best Location Studio In Downtown Boston
Front of property
Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2.0 star property
Beacon Hill
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
$182 nightly
The price is $210
Dec 17 - Dec 18
Total with taxes and fees
Maverick Suites at 40 Temple St
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (322)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
$175 nightly
The price is $202
Dec 8 - Dec 9
Total with taxes and fees
Maverick Suites at 28 Fenway
TV, offices
Come Visit Boston and Stay In Our Homey Studio

Come Visit Boston and Stay In Our Homey Studio

Downtown Boston
8.8 out of 10, Excellent, (3)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
$183 nightly
The price is $215
Dec 8 - Dec 9
Total with taxes and fees
Come Visit Boston and Stay In Our Homey Studio
Exterior
North End Gem ★ Prime Location + Parking Included

North End Gem ★ Prime Location + Parking Included

North End
9.6 out of 10, Exceptional, (58)
"Had a very nice time close to everything walking distance to alot of fun and exciting things "
United States
Lynn W.
North End Gem ★ Prime Location + Parking Included
1 bedroom, desk, iron/ironing board, WiFi
Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!

Bay Village
10.0 out of 10, Exceptional, (4)
"Would stay again"
United States
mark p.
$183 nightly
The price is $215
Dec 16 - Dec 17
Total with taxes and fees
Studio Awaits Your Next Stay!
Desk, iron/ironing board, WiFi, bed sheets
The Chester: Urban Chic Retreat In South End

The Chester: Urban Chic Retreat In South End

2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"
United States
Chad T.
$328 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
The Chester: Urban Chic Retreat In South End
1 bedroom, WiFi
Modern North End Studio

Modern North End Studio

North End
9.0 out of 10, Wonderful, (10)
"Convenient location. Great restaurants. Perfect apatment for a couple. "
United States
Holly V.
$270 nightly
The price is $310
Dec 9 - Dec 10
Total with taxes and fees
Modern North End Studio
1 bedroom, desk, iron/ironing board, WiFi
Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!

Downtown Boston
8.6 out of 10, Excellent, (17)
"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"
United States
Christine
$186 nightly
The price is $218
Dec 8 - Dec 9
Total with taxes and fees
Perfect One Bedroom Stay In Downtown Boston!
Private kitchen
Perfetto North End 1brm

Perfetto North End 1brm

North End
10.0 out of 10, Exceptional, (11)
"The location was perfect - we would stay here again.The description and pictures are accurate."
United States
Kenna E.
$305 nightly
The price is $351
Dec 28 - Dec 29
Total with taxes and fees
Perfetto North End 1brm
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

The Chester Hotel

4.0 star property
South End
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
$305 nightly
The price is $351
Dec 8 - Dec 9
Total with taxes and fees
The Chester Hotel
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
"Room was great. Staff was great too. We were quite happy with everything. The only thing I needed was an outlet next to the bed."
Carlyn 2-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 $144 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?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This vacation home rental outside of Wellesley is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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?

Family-friendly attractions include Massachusetts Horticultural Society's Gardens at Elm Bank, whereas Charles River is a spot to enjoy the outdoors. Other popular places to visit in the area include Fenway Park and Harvard Square.

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.