Wellesley Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Wellesley vacation rentals

Exterior
Spacious Private Entrance Master Bedroom/Bath

Apartment in Wellesley

Spacious Private Entrance Master Bedroom/Bath
10.0 out of 10, Exceptional, (90)
"Great place to stay. "
United States
Alexa
$142 nightly
The price is $156
Jan 12 - Jan 13
Total with taxes and fees
Spacious Private Entrance Master Bedroom/Bath
Exterior
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Charlestown

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
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.
$377 nightly
The price is $433
Jan 7 - Jan 8
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Property grounds
Charlestown Houseboat Walk to attractions Be rocked to sleep

Houseboat in Thompson Square - Bunker Hill

Charlestown Houseboat Walk to attractions Be rocked to sleep
9.6 out of 10, Exceptional, (99)
"Great location, pet friendly, "
United States
Karen W.
$354 nightly
The price is $407
Jan 7 - Jan 8
Total with taxes and fees
Charlestown Houseboat Walk to attractions Be rocked to sleep
Interior
Fun houseboat. Walk to Boston attractions WIFI

Houseboat in Boston

Fun houseboat. Walk to Boston attractions WIFI
9.8 out of 10, Exceptional, (89)
"It was unique way to stay in the city"
United States
brian m.
$377 nightly
The price is $433
Jan 7 - Jan 8
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (329)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
$155 nightly
The price is $178
Jan 7 - Jan 8
Total with taxes and fees
Temple Place Suites
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (134)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
$175 nightly
The price is $201
Feb 6 - Feb 7
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.6 out of 10, (252)
"Great location nice neighborhood "
United States
Jose
$145 nightly
The price is $167
Jan 7 - Jan 8
Total with taxes and fees
Bay Village Suites
Lobby lounge
Global Luxury Suites Downtown Boston

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (639)
"Very clean, beautiful place. I would stay there again."
Canada
Liam
$128 nightly
The price is $147
Jan 11 - Jan 12
Total with taxes and fees
Global Luxury Suites Downtown Boston
Front of property
Maverick Suites at 40 Temple St

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (103)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
$194 nightly
The price is $223
Jan 7 - Jan 8
Total with taxes and fees
Maverick Suites at 40 Temple St
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (256)
"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"
United States
Aziza
$133 nightly
The price is $153
Jan 19 - Jan 20
Total with taxes and fees
Premier Suites - Bay Village
Exterior
Maverick Suites at 245 Newbury St

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very Good, (155)
"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 11 - Jan 12
Total with taxes and fees
Maverick Suites at 245 Newbury St
Front of property
Maverick Suites at 28 Fenway

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (333)
"Good place"
United States
Elijah
$190 nightly
The price is $218
Jan 7 - Jan 8
Total with taxes and fees
Maverick Suites at 28 Fenway
Premium Apartment | Living area | 24-inch Smart TV with digital channels
The Chester Hotel

Aparthotel in South End

The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
$264 nightly
The price is $304
Jan 10 - Jan 11
Total with taxes and fees
The Chester Hotel
Iron/ironing board, WiFi, bed sheets
The Chester: Hip, Renovated, South End

Apartment in South End

The Chester: Hip, Renovated, South End
2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
$253 nightly
The price is $290
Jan 7 - Jan 8
Total with taxes and fees
The Chester: Hip, Renovated, South End
Exterior
Perfect Studio, Walk To Park!

Apartment in Downtown Boston

Perfect Studio, Walk To Park!
7.2 out of 10, Good, (7)
"Perfect location in downtown crossing near the common, with lots to do on the same block as the apartment."
United States
Tim G.
$183 nightly
The price is $215
Jan 12 - Jan 13
Total with taxes and fees
Perfect Studio, Walk To Park!
TV, offices
Come Visit Boston and Stay In Our Homey Studio

Apartment in Downtown Boston

Come Visit Boston and Stay In Our Homey Studio
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
Jan 12 - Jan 13
Total with taxes and fees
Come Visit Boston and Stay In Our Homey Studio
Apartment | 1 bedroom, desk, laptop workspace, free WiFi
Furnished Apartments near Encore Boston

Aparthotel in Everett

Furnished Apartments near Encore Boston
2.5 star property
8.6 out of 10, Excellent, (9)
"Great place. Very clean. Great communication."
United States
Michele
$190 nightly
The price is $213
Jan 8 - Jan 9
Total with taxes and fees
Furnished Apartments near Encore Boston
Exterior
Walk to Boston Common, Safe & Central Stay

Apartment in Beacon Hill

Walk to Boston Common, Safe & Central Stay
7.2 out of 10, Good, (17)
"Property was excellent. Transportation was easy and communication with host was great. Thanks for a great vacation in beautiful Boston."
United States
john
$225 nightly
The price is $265
Jan 8 - Jan 9
Total with taxes and fees
Walk to Boston Common, Safe & Central Stay
Interior entrance
Maverick Suites at 89 Marion

Aparthotel in Coolidge Corner South Side

Maverick Suites at 89 Marion
2.0 star property
8.2 out of 10, Very Good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
$182 nightly
The price is $203
Jan 7 - Jan 8
Total with taxes and fees
Maverick Suites at 89 Marion
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Aparthotel in Fenway–Kenmore

Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
$286 nightly
The price is $329
Jan 7 - Jan 8
Total with taxes and fees
Charlesgate Suites
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

Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"The room was spacious! Great housekeeping. The location is also great! "
andre 3-night trip
Posted 14 hours ago
Hyatt Regency 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 $121 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 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.