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

Westwood Holiday Rentals

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Our top choices for Westwood holiday rentals

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, (4 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is NZ$511
includes taxes & fees
4 Nov - 5 Nov
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

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, (70 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
The price is NZ$406
includes taxes & fees
28 Oct - 29 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

3. Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.6 out of 10, Exceptional, (31 reviews)
"This rental is truly exceptional! If I could, I’d give it a ten star rating. The property was spotlessly clean and very comfortable, with many unexpected and thoughtful touches. Our host Delphine was lovely - easily accessible and welcoming. We will definitely return here when we are in the area!"
United States
Erika D.
The price is NZ$404
includes taxes & fees
7 Oct - 8 Oct
Charming 2-bedroom apartment with WiFi, AC in superb Canton

4. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,297 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is NZ$266
includes taxes & fees
1 Nov - 2 Nov
Crescent Suites Hotel

5. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (93 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
The price is NZ$581
includes taxes & fees
5 Oct - 6 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖

6. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (206 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is NZ$624
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 245 Newbury St

7. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.4 out of 10, Good, (26 reviews)
"Cute space! Wasn’t too difficult navigating Boston from this location."
United States
Rebecca
The price is NZ$723
includes taxes & fees
27 Oct - 28 Oct
The Concord Hotel

8. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (326 reviews)
"Room was clean, neat area."
United States
Keir
The price is NZ$434
includes taxes & fees
5 Oct - 6 Oct
Maverick Suites at 89 Marion

9. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (17 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
The price is NZ$418
includes taxes & fees
4 Nov - 5 Nov
Stunning Back Bay Studio Apartment

10. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (39 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is NZ$663
includes taxes & fees
5 Oct - 6 Oct
The Chester Hotel

11. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (490 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is NZ$310
includes taxes & fees
2 Nov - 3 Nov
Temple Place Suites

12. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (434 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is NZ$449
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway

13. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (357 reviews)
"Great spot, Clean, quiet, and convenient. Perfect no frills, no hassle spot in Boston. And very reasonably priced these days!"
United States
Ed
The price is NZ$289
includes taxes & fees
3 Nov - 4 Nov
Premier Suites - Bay Village

14. 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, (58 reviews)
"Great overall stay!"
United States
Chris R.
The price is NZ$902
includes taxes & fees
6 Oct - 7 Oct
Cozy three-bedroom home close to Boston w/ plenty of parking

15. Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (53 reviews)
"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"
United States
Alicia R.
The price is NZ$643
includes taxes & fees
6 Oct - 7 Oct
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

16. 60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
Mattapan
9.6 out of 10, Exceptional, (29 reviews)
"Perfect home. Great location. Would recommend!!!!"
United States
Nicole M.
The price is NZ$700
includes taxes & fees
5 Oct - 6 Oct
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

17. Modern Studio | South End

Modern Studio | South End
Back Bay
"The location was PERFECT! Very walkable, safe and close to the subway. Exceptional communication! We will chose to stay here again when in Boston."
United States
Lori
The price is NZ$373
includes taxes & fees
1 Nov - 2 Nov
Modern Studio | South End

18. 4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

4BR 6BEDS WOLLASTON BEACH. NearBOSTON3
Quincy
10.0 out of 10, Exceptional, (46 reviews)
"Kim was great in regards to communication and and answered all my questions and was very accommodating! We enjoyed our stay and the kids loved playing at the beach too as it was a couple minute walk :) Theres a playground nearby which helped out a lot too!"
United States
Jennifer V.
The price is NZ$1,454
includes taxes & fees
20 Oct - 21 Oct
4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

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

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.4 out of 10, Very good, (15 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
The price is NZ$575
includes taxes & fees
8 Oct - 9 Oct
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

20. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (152 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is NZ$401
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 40 Temple St
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

Find out more about Westwood

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Westwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Westwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Westwood. Seeing all the best attractions is bound to make you fall in love with Westwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Westwood short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Westwood?

Yes, there are holiday rentals close to the most popular sights in Westwood, or you can select a more secluded 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 holiday rentals that Westwood has to offer?

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

How many holiday rentals will I find in Westwood?

With 5 Expedia holiday rentals, you're guaranteed 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 such as Gillette Stadium and Fenway Park.

What are holiday rentals like in Westwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westwood. Holiday rentals offer amenities such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.