A white church with a steeple and green shutters, surrounded by trees and a clear blue sky.

Westwood Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Westwood vacation rentals

A spacious living area with a fireplace, a large window, and a kitchen area with modern appliances.

1. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (8 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
$277 nightly
The price is $309
Nov 21 - Nov 22
Total with taxes and fees
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A gazebo with a stone barbecue grill and a table with chairs.

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

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (74 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
$197 nightly
The price is $220
Nov 15 - Nov 16
Total with taxes and fees
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A pathway leading to a stone bench surrounded by trees with yellow leaves. A sign requests the use of the sidewalk for access to Charles River.

3. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,358 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
$140 nightly
The price is $157
Dec 13 - Dec 14
Total with taxes and fees
Crescent Suites Hotel
A wooden hallway with a patterned floor leading to a door.

4. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (357 reviews)
"The area was walkable and the room was great!"
United States
Edna
$159 nightly
The price is $178
Nov 15 - Nov 16
Total with taxes and fees
Maverick Suites at 89 Marion
A covered outdoor area with a 'hello' sign, potted plants, and a view into the interior.

5. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"We had a great visit and the house gave us everything we needed for a comfortable stay. The rooms were nicely furnished and the bedrooms were spacious. The location was convenient for accessing the bus and the subway. The host was very friendly and responsive. We hope to visit again!"
United States
Christina B.
$477 nightly
The price is $548
Nov 23 - Nov 24
Total with taxes and fees
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A row of brick buildings with storefronts, including a bakery and a liquor store.

6. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
$168 nightly
The price is $193
Dec 2 - Dec 3
Total with taxes and fees
Maverick Suites at 245 Newbury St
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
$247 nightly
The price is $284
Nov 23 - Nov 24
Total with taxes and fees
The Chester Hotel
A room with a bed, a round table, chairs, a large mirror, and a view of greenery outside.

8. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.2 out of 10, Very good, (41 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
$231 nightly
The price is $266
Nov 24 - Nov 25
Total with taxes and fees
The Concord Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

9. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (169 reviews)
"great location near the commons. nice space for single traveler."
United States
Andrea
$151 nightly
The price is $173
Dec 1 - Dec 2
Total with taxes and fees
Maverick Suites at 40 Temple St
A wooden deck with white railings, a glass door, and a metal awning.

10. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.6 out of 10, Exceptional, (11 reviews)
"Amazing place and great host!"
United States
Harmoni C.
$180 nightly
The price is $207
Nov 16 - Nov 17
Total with taxes and fees
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

11. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (401 reviews)
"Good place to stay."
United States
Jaetaek
$125 nightly
The price is $144
Dec 14 - Dec 15
Total with taxes and fees
Premier Suites - Bay Village
A multi-story hotel with a classic architectural style, featuring arched windows and a central entrance.

12. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (776 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
$201 nightly
The price is $231
Dec 13 - Dec 14
Total with taxes and fees
Global Luxury Suites Downtown Boston
A brick building with a green awning labeled "The UPS Store" and a door marked "402".

13. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (186 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
$159 nightly
The price is $183
Nov 15 - Nov 16
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

14. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (479 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
$186 nightly
The price is $214
Nov 15 - Nov 16
Total with taxes and fees
Maverick Suites at 28 Fenway
An outdoor patio area with wooden furniture, string lights, and a bar area.

15. 🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (126 reviews)
"What a gorgeous historical property! We found this to be perfect for our group of four. Loved that it had two restrooms."
United States
grwilly00
$329 nightly
The price is $378
Nov 19 - Nov 20
Total with taxes and fees
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

16. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
9.0 out of 10, Wonderful, (25 reviews)
"Great location."
United States
Chloe
$168 nightly
The price is $197
Dec 8 - Dec 9
Total with taxes and fees
Stunning Back Bay Studio Apartment
A living room with a television on a stand, a fireplace, a bottle of wine, and two wine glasses on a table.

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

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (11 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
$190 nightly
The price is $212
Dec 1 - Dec 2
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A wooden deck with a lattice railing, two wooden chairs, and a glass door leading to a room.

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

Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
Watertown
9.8 out of 10, Exceptional, (65 reviews)
"I was very satisfied with my stay at this property. Mehmet, our host, made sure that we had everything we needed to make our stay comfortable. If I returned to this area, I would definitely stay here again."
United States
Melissa F.
$177 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A brick building with a dark door, steps leading up to a porch, and potted plants on the ground floor.

19. Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Beacon Hill
9.6 out of 10, Exceptional, (10 reviews)
"Great location!"
United States
Lea M.
$315 nightly
The price is $362
Nov 24 - Nov 25
Total with taxes and fees
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
A kitchen with a dining table, chairs, and a countertop with a vase of flowers.

20. Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (61 reviews)
"Great overall stay!"
United States
Chris R.
$385 nightly
The price is $429
Nov 16 - Nov 17
Total with taxes and fees
Cozy three-bedroom home close to Boston w/ plenty of parking
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 Westwood Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Great amenities"
Abigail 1-night trip
Posted less than an hour ago
Omni Boston Hotel at the Seaport

Find out more about Westwood

Everything you need to know about Westwood 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 Westwood 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 Westwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westwood. 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 Westwood 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 Westwood rentals

At Expedia, we put the best Westwood 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 Westwood 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 Westwood 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 Westwood. 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 Westwood?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Westwood, or you can select a more remote option if you're looking for a relaxing stay. Westwood is known for its restaurants and shopping. Make sure you have time to check out the monuments and sporting events during your trip.

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: Visitors like this Westwood vacation home rental. It has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Westwood?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Westwood stay.

What can I see and do in Westwood?

Explore the area and family-friendly sights such as The Skating Club of Boston, or get out into nature at a spot like Charles River. While in the area, you can also visit popular places like Gillette Stadium and Fenway Park.

What are vacation rentals like in Westwood?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Westwood. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.