Wellesley Vacation Rentals from CA $87: Short-Term Rentals for 2026

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Our top choices for Wellesley vacation rentals

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

1. Crescent Suites Hotel

South Side

Kasandra

CA $223 total

includes taxes & fees

Nov 21 - Nov 22

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

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

Framingham

roger n.

CA $300 total

includes taxes & fees

Nov 11 - Nov 12

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

3. Maverick Suites at 89 Marion

Coolidge Corner

Edna

CA $288 total

includes taxes & fees

Dec 1 - Dec 2

A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

4. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Framingham

Jessica D.

CA $519 total

includes taxes & fees

Nov 30 - Dec 1

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

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

Dedham

Cortney

CA $300 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Watertown

Melissa F.

CA $325 total

includes taxes & fees

Nov 9 - Nov 10

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

7. Maverick Suites at 28 Fenway

Fenway–Kenmore

Judy

CA $305 total

includes taxes & fees

Dec 1 - Dec 2

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

8. Global Luxury Suites Downtown Boston

Chinatown

Yelitza

CA $327 total

includes taxes & fees

Nov 29 - Nov 30

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

9. The Chester Hotel

South End

Tracy

CA $413 total

includes taxes & fees

Nov 9 - Nov 10

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

10. The Concord Hotel

South End

Rupintal

CA $439 total

includes taxes & fees

Nov 11 - Nov 12

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

11. Premier Suites - Bay Village

Bay Village

Jaetaek

CA $210 total

includes taxes & fees

Nov 23 - Nov 24

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

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

Fenway–Kenmore

Jay G.

CA $292 total

includes taxes & fees

Nov 15 - Nov 16

A living room with a sofa, armchair, coffee table, TV, cabinet, and artwork.

13. Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

Ward Two

Mike w.

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

14. Kasa Boston at Fenway

Fenway–Kenmore

antonio

CA $419 total

includes taxes & fees

Nov 23 - Nov 24

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

15. Stunning Back Bay Studio Apartment

Back Bay

Chloe

CA $266 total

includes taxes & fees

Dec 7 - Dec 8

16. Modern Studio | South End

Back Bay

Kaylee P.

CA $273 total

includes taxes & fees

Nov 16 - Nov 17

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

17. Maverick Suites at 245 Newbury St

Back Bay

Chloe

CA $314 total

includes taxes & fees

Dec 6 - Dec 7

18. Stellar South End Studio

Back Bay

Beth

CA $316 total

includes taxes & fees

Nov 22 - Nov 23

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

19. Maverick Suites at 40 Temple St

Beacon Hill

Andrea

CA $314 total

includes taxes & fees

Dec 1 - Dec 2

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a large window providing natural light.

20. Beautiful 1BR near Fenway Park + Kenmore!

Fenway–Kenmore

mariia

CA $345 total

includes taxes & fees

Nov 12 - Nov 13

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Top Wellesley Hotel Reviews

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

HYATT house Boston/Waltham

Waltham

10/10 Excellent

Eddie

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

Fairfield Inn & Suites by Marriott Boston Waltham

Waltham

10/10 Excellent

Daniel

A courtyard with a fire pit, outdoor seating, and a brick building in the background.

Courtyard by Marriott Boston Waltham

Piety Corner

10/10 Excellent

Florencia

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

Cambria Hotel Boston Somerville

Spring Hill

10/10 Excellent

Li

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

Arcadian Hotel

Coolidge Corner

10/10 Excellent

Stéfanie

A modern living room with a sofa, a dining table, and chairs. There is a kitchen area with cabinets and a microwave.

Sonesta Simply Suites Boston Burlington

Burlington

10/10 Excellent

Guillaume

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

citizenM Boston Back Bay

Fenway–Kenmore

10/10 Excellent

Very fabulous hotel, combination of Scandinavian functionality and aesthetics. Everything in the room (tiny, but not as tiny as a Japanese hotel room) is so well-thought out. The iPad controls everything in the room: lights, curtains, TV, temperature etc. The night curtain truly blacks out the room. The mattress is not saggy - super comfortable. The light in the bathroom changes colour on command; there’s also a memory game to play (“Marvin” changes the colour of the light and you have to...

Constant

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

Iris Hotel Boston

Coolidge Corner

10/10 Excellent

Tracy

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

DoubleTree Suites by Hilton Hotel Boston - Cambridge

Allston

10/10 Excellent

Amber

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.

Hotel 1868

Agassiz

10/10 Excellent

Leilani

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 $87 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.

Wellesley Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wellesley vacation rentals

1. Crescent Suites Hotel

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

3. Maverick Suites at 89 Marion

4. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

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

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

7. Maverick Suites at 28 Fenway

8. Global Luxury Suites Downtown Boston

9. The Chester Hotel

10. The Concord Hotel

11. Premier Suites - Bay Village

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

13. Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

14. Kasa Boston at Fenway

15. Stunning Back Bay Studio Apartment

16. Modern Studio | South End

17. Maverick Suites at 245 Newbury St

18. Stellar South End Studio

19. Maverick Suites at 40 Temple St

20. Beautiful 1BR near Fenway Park + Kenmore!

Find vacation rentals that suit your style

Top Wellesley Hotel Reviews

HYATT house Boston/Waltham

10/10 Excellent

Find out more about Wellesley

Wellesley vacation rentals: An excellent choice for every season

How to find incredible deals on Wellesley rentals

Frequently Asked Questions

Can I find vacation rentals in Wellesley?

What are some of the best vacation rentals that Wellesley has to offer?

How many vacation rentals are there in Wellesley?

What can I see and do in Wellesley?

What are vacation rentals like in Wellesley?