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A church with a tall steeple, surrounded by autumn-colored trees and residential buildings.

Wellesley Vacation Rentals

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Wellesley vacation rentals

    1. Crescent Suites Hotel

    An outdoor patio with round tables and chairs, surrounded by green umbrellas.

    2. Maverick Suites at 89 Marion

    A wooden hallway with a patterned floor leading to a door.

    3. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

    A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

    4. Maverick Suites at 245 Newbury St

    A row of brick buildings with storefronts, including a bakery and a liquor store.

    5. Maverick Suites at 40 Temple St

    A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

    6. Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston

    A bedroom with a bed, nightstands, a window, and a ceiling fan.

    7. Global Luxury Suites Downtown Boston

    A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

    8. Maverick Suites at 28 Fenway

    A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

    9. Premier Suites - Bay Village

    A modern bedroom with a large bed, a fireplace, and two windows with blinds.

    10. The Chester Hotel

    A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

    11. The Concord Hotel

    A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

    12. Maverick Suites at 400 Columbus Ave

    A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

    13. Stunning Back Bay Studio Apartment

    A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

    14. Kasa Boston at Fenway

    A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

    15. Temple Place Suites

    A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

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

    A brick building with a black front door, a staircase, and a well-maintained garden.

    17. Modern Studio | South End

    A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

    18. Stellar South End Studio

    A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

    19. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

    A gazebo with a stone barbecue grill and a table with chairs.

    20. Charlesgate Suites

    A modern hotel room with a bed, a desk, a sofa, and a dining area.

    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

    Hilton Garden Inn Boston/Waltham

    A modern café with a chilled beverage fridge, a frozen section, and a variety of snacks and drinks.

    HYATT house Boston/Waltham

    An outdoor patio area with a fire pit, seating, and a grill.

    Fairfield Inn & Suites by Marriott Boston Waltham

    A modern living room with a fireplace, sofas, a dining area, and a TV mounted above the fireplace.

    Copley House

    A building with a brick facade partially covered in green ivy.

    Hilton Garden Inn Boston Canton

    A covered outdoor seating area with stone walls, green sofas, and a central fire feature.

    Cambria Hotel Boston Somerville

    A modern bar area with a long counter, multiple seating options, and large windows providing views of the outside.

    citizenM Boston Back Bay

    A bar area with a city view, bar stools, and a bar counter.

    Hotel 1868

    A cozy living room with a leather sofa, a white armchair, and a coffee table. There are framed botanical illustrations on the wall and a large window with hanging glass terrariums.

    DoubleTree Suites by Hilton Hotel Boston - Cambridge

    A transparent dome structure with a metal framework, a glass floor, and a metal railing.

    citizenM Boston North Station

    A modern living room with a sofa, a coffee table, and a bookshelf filled with books and decorative items.

    Iris Hotel Boston

    A hotel room with two beds, a round table with chairs, a TV, and large windows with curtains.

    The Godfrey Hotel Boston

    A restaurant interior with wooden tables, a bar area, and a mural on the wall.

    Harborside Inn Of Boston

    An outdoor cafe with tables and chairs, a building entrance, and a street sign.

    Arcadian Hotel

    A spacious indoor area with a high ceiling, multiple seating arrangements, and a bar area.

    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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wellesley vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Wellesley vacation rentals we have selected for you start as low as CA $100 per night. Entering your travel dates in the search wizard 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.

    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?

    Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: This vacation home rental outside of Wellesley has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

    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.