First Baptist Church at 808 High Street in historic town center of Westwood, Massachusetts MA, USA.

Holiday Rentals in Westwood

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Our top choices for Westwood holiday rentals

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, (1 review)
"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 €194
includes taxes & fees
1 Jul - 2 Jul
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Thompson Square - Bunker Hill
10.0 out of 10, Exceptional, (63 reviews)
"Really loved our stay here. The room was well stocked with everything we could need and more. Would definitely book here again! "
United States
Daniel S.
The price is €497
includes taxes & fees
13 Jul - 14 Jul
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Endless Summer: Oceanside Views

Endless Summer: Oceanside Views
Boston
10.0 out of 10, Exceptional, (42 reviews)
"This is a great location and very unique property. Perfect for my husband and I"
United States
Anonymous traveller
The price is €589
includes taxes & fees
6 Jul - 7 Jul
Endless Summer: Oceanside Views

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
Boston
10.0 out of 10, Exceptional, (123 reviews)
"Overall our stay was good!"
United States
Yan B.
"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (105 reviews)
"host was so welcoming and we enjoyed they stay"
United States
Roshawn D.
The price is €598
includes taxes & fees
1 Jul - 2 Jul
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (635 reviews)
"Excellent location and clean room with beautiful views. Very comfortable and convenient."
United States
Noelle
The price is €322
includes taxes & fees
20 Jun - 21 Jun
Marriott Vacation Club® at Custom House, Boston

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (707 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is €253
includes taxes & fees
6 Jul - 7 Jul
Global Luxury Suites Downtown Boston

Bright 1 Bedroom | Downtown Boston

Bright 1 Bedroom | Downtown Boston
Bay Village
10.0 out of 10, Exceptional, (1 review)
"Great location to explore Boston with your dogs"
Canada
Thiery
The price is €270
includes taxes & fees
6 Jul - 7 Jul
Bright 1 Bedroom | Downtown Boston

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (37 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is €946
includes taxes & fees
30 Jun - 1 Jul
The Monty Boston

Boston Financial District 1BR | Walk to anything!

Boston Financial District 1BR | Walk to anything!
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"The room was great, for what little time we spent in it, it was a really cozy place. The bed was huge, and really comfortable, I loved how much light the place got as well, with the windows. We were slightly off put by the pictures of the place with how incredibly beige the place looked, but I can assure you it looks way better in person lol. The location is great as well, I've never been to a city this walkable, so I'm glad we picked somewhere right in the middle of it, almost every direction...
United States
Kyle
The price is €382
includes taxes & fees
2 Jul - 3 Jul
Boston Financial District 1BR | Walk to anything!

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (288 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is €377
includes taxes & fees
20 Jun - 21 Jun
Kasa Boston at Fenway

Downtown Studio | Students Welcome | W/D in unit

Downtown Studio | Students Welcome | W/D in unit
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Was worth the price all around"
United States
steven l.
The price is €308
includes taxes & fees
24 Jun - 25 Jun
Downtown Studio | Students Welcome | W/D in unit

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very good, (2 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is €314
includes taxes & fees
30 Jun - 1 Jul
Symple Live

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
The price is €222
includes taxes & fees
6 Jul - 7 Jul
Light-filled Studio | Back Bay

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (292 reviews)
"Great location and well maintained"
United States
EDDIE
The price is €165
includes taxes & fees
24 Jun - 25 Jun
Premier Suites - Bay Village

King Bed Loft in the Heart of Downtown Boston

King Bed Loft in the Heart of Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (42 reviews)
"Roomy, clean, all the amenities that we needed and Aaron was a wonderful host! Pictures are accurate and location is easy walking is such a wonderful city. Thanks Aaron!"
United States
James L.
King Bed Loft in the Heart of Downtown Boston

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (214 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is €330
includes taxes & fees
21 Jun - 22 Jun
Charlesgate Suites

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Fenway–Kenmore
10.0 out of 10, Exceptional, (2 reviews)
"Great location with comfortable accommodations!! Easy access to great restaurants, Fenway, and the T. Host provided excellent communication and was extremely responsive. Highly recommend!"
United States
Andrea G.
The price is €372
includes taxes & fees
6 Jul - 7 Jul
Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.8 out of 10, Excellent, (11 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
The price is €367
includes taxes & fees
1 Jul - 2 Jul
Stylish Back Bay Retreat, Steps from Prudential

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, (9 reviews)
"It was a great place. Good location, clean, comforable and the host was quick with a few questions that we had. "
United States
Heather A.
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
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

Everything you need to know about Westwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Westwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Westwood holiday 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 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 Westwood holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westwood holiday rentals we have selected for you start as low as €126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Westwood rentals

At Expedia, we put the best Westwood holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Westwood?

Yes, we have holiday rentals where you'll be just 13.4 mi (21.6 km) from New England Aquarium, giving you a more secluded option to escape the hustle and bustle. 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?

Boston's Best Vacation Home : This holiday home rental outside of Westwood is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

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 New England Aquarium, 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.