Wellesley Vacation Rentals from $155: Search Short-Term Rentals

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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

kari

$139 nightly

Nov 5 - Nov 6

Total with taxes and fees

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.

$210 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

3. Maverick Suites at 89 Marion

Coolidge Corner

Edna

$193 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a large bed, a smaller bed, a nightstand with a lamp, a mirror, and a window with a view of greenery.

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

Watertown

Melissa F.

$212 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

5. The Chester Hotel

South End

Luda

$246 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

6. Kasa Boston at Fenway

Fenway–Kenmore

Krista

$270 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Dedham

Cortney

$203 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

8. Premier Suites - Bay Village

Bay Village

Rosemary

$152 nightly

Nov 2 - Nov 3

Total with taxes and fees

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.

9. Maverick Suites at 400 Columbus Ave

South End

Lorne

$193 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

10. Maverick Suites at 245 Newbury St

Back Bay

Jennifer

$240 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Framingham

Michelle M.

$341 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

12. The Concord Hotel

South End

Rupintal

$276 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

13. Maverick Suites at 28 Fenway

Fenway–Kenmore

Beenish

$212 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

14. Charlesgate Suites

Fenway–Kenmore

Svetlana

$322 nightly

Nov 22 - Nov 23

Total with taxes and fees

A bedroom with a bed, a chair, a desk, a radiator, and a ceiling fan.

15. Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Fenway–Kenmore

Matthew G.

$283 nightly

Oct 26 - Oct 27

Total with taxes and fees

A living room with a fireplace, a green sofa, a dining table with chairs, and a large window.

16. Cozy & Modern 1 BDR | Fenway within minutes!

Fenway–Kenmore

Dean B.

$229 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

17. Temple Place Suites

Downtown Boston

Deborah

$144 nightly

Nov 22 - Nov 23

Total with taxes and fees

A spacious room with a wooden floor, a white door, and a large window with a view of a staircase.

18. The Harvard Room conveniently near BC & Harvard

Brighton

Michael D.

$309 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern hotel lobby with a seating area, a bar, and a kitchen.

19. Residences at Solomon Pond

Marlborough

Huynh

$106 nightly

Oct 27 - Oct 28

Total with taxes and fees

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

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

Fenway–Kenmore

Samantha

$215 nightly

Nov 1 - Nov 2

Total with taxes and fees

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Top Wellesley Hotel Reviews

The Revolution Hotel

10/10 Excellent

"Awesome staff, clean rooms, great area of town"

Hyatt Regency Boston Harbor

8/10 Good

"Far from downtown Boston so you will need to figure out transportation into the city and back. No restaurant's or shopping nearby. The television in our room was not working correctly. At one point, I had to unplug it from the back because I could hear the sound but there was nothing on the screen. Otherwise, the breakfast buffet was really good each morning."

Seaport Hotel Boston

8/10 Good

"Everything was great at the hotel except for our initial check-in person. She was working on something and didn’t even look up for quite a while and then told us she would be with us in a minute, and we waited even longer. Seemed like she could have stopped & acknowledged us right away. The gentleman taking luggage to our room was super friendly& a great face for the hotel."

The Dagny Boston

8/10 Good

"For an expensive hotel, I was hoping for a little more. However, it seems all Boston hotels are expensive. For £400 per night, one would expect top notch. Very good but not exceptional, and why does the music have to be so loud in the lobby, even at 6.30 in the morning. I feel for the staff as much as the clientele."

Bedford Plaza Hotel - Boston

8/10 Good

"The staff was great. The hotel definitely needs to be remodeled. Rugs are stained and worn. Everything is just old and worn. Bed was good though, pillows not so much. We didn't have towels in our room so we had to hunt for the maid the next morning to get some. The free breakfast consists of waffles, toast, cereal and yogurt. I had booked a last minute trip so my options at the time were not plentiful. If you just need a place to lay your head at the end of the day like we did, you should be fine."

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 $155 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.

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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

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

5. The Chester Hotel

6. Kasa Boston at Fenway

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

8. Premier Suites - Bay Village

9. Maverick Suites at 400 Columbus Ave

10. Maverick Suites at 245 Newbury St

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

12. The Concord Hotel

13. Maverick Suites at 28 Fenway

14. Charlesgate Suites

15. Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

16. Cozy & Modern 1 BDR | Fenway within minutes!

17. Temple Place Suites

18. The Harvard Room conveniently near BC & Harvard

19. Residences at Solomon Pond

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

Find vacation rentals that suit your style

Top Wellesley Hotel Reviews

The Revolution Hotel

Find out more about Wellesley

Explore a world of travel with Expedia

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