Holiday Homes in Westwood

Featured Holiday Homes in Westwood

Peaceful 2Br House in Cambridge

2.0 star property
10.0 out of 10, Exceptional, (1)
"The location was great for us to visit our college student in Boston. Peaceful & quiet neighborhood. Our host was great in responding to any questions/issues we had."
Peaceful 2Br House in Cambridge

New 5B3B Single Family with Central AC

9.8 out of 10, Exceptional, (20)
"My parents live in town so it was lovely to have all my family to stay at this Vrbo and be able to celebrate with my Dad! The house was perfect..the rooms were spacious and the kitchen bathroom areas were so clean! The host was very accommodating and communicated with me very quickly!"
New 5B3B Single Family with Central AC

Spacious & Convenient 1BR unit-20min to Boston

2.0 star property
9.8 out of 10, Exceptional, (6)
"Property was perfect size for couple or small family. Located close resturants and Shopping. Just a short drive to Boston and neighboring towns. Highly recommend. Host was very responsive to all messages."
The price is AU$667
includes taxes & fees
24 Nov - 25 Nov
Spacious & Convenient 1BR unit-20min to Boston

Newly renovated home, top of the line appliances.

9.8 out of 10, Exceptional, (109)
"The house was beautiful, clean, spacious with everything we needed. Loved it."
Newly renovated home, top of the line appliances.

Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs

7.0 out of 10, Good, (21)
"It's in a basement and there was a door to another part of the basement that was locked and we could see a light that was on all night on the other side. It was very quiet though, great if you just need somewhere to sleep."
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs

CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

2.0 star property
9.6 out of 10, Exceptional, (12)
"The Chelsea house is a great place to stay. It is a great location to visit Boston. There are some local eateries within walking distance plus a Dunkin Donuts. The house was very clean and had all the amenities you’d need. The bedrooms are on the second and third floors. I would definitely stay here again. "
The price is AU$794
includes taxes & fees
9 Dec - 10 Dec
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

Lovely Cape Cod Style Home ~ Close To Boston ~ Hot Tub ~ Steps To Walking Trails

9.8 out of 10, Exceptional, (35)
"We gathered from around the Country and this home exceeded our expectations! Plenty of space to gather together but space to be alone when needed. Everyone was happy with bed comfort and bedding. Plenty of supplies for group meal prep. Nantasket Beach and Hingham ferry both less then 15 mins. away. Worlds End is practically in the backyard. Really enjoyed this property and would book again!"
Lovely Cape Cod Style Home ~ Close To Boston ~ Hot Tub ~ Steps To Walking Trails

Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

2.0 star property
9.4 out of 10, Exceptional, (3)
"It was a cute property. About a 15 minute Uber from anything you want to do. We had trouble getting the lock to open and couldn’t get the host to answer the phone but the neighbor helped us!"
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

Union Square House

9.6 out of 10, Exceptional, (66)
"Location was super convenient, shower was excellent. Leftover foods in cabinets and fridge were a bit unexpected. "
Union Square House

Bright & Pet-Friendly Home: 2 Mi to Harvard Square

10.0 out of 10, Exceptional, (10)
"The property was clean and well cared for - enjoyed our stay. Lots of room."
Bright & Pet-Friendly Home: 2 Mi to Harvard Square

Wonderful Renovated Family Friendly Home Close to Boston and Lexington

10.0 out of 10, Exceptional, (60)
"We enjoyed our stay and Janel was very responsive which we appreciated. The house was well appointed and our son especially enjoyed the children’s room with a “secret”closet full of books and toys. "
Wonderful Renovated Family Friendly Home Close to Boston and Lexington

Spacious 2BR 2BA Condo & 2x Parking, Minutes from Central Sq, MIT, Harvard.

9.0 out of 10, Wonderful, (11)
"Loved staying here. The place is just as described. Lots of room, each bedroom has its own bathroom. Will be staying here next time we're in town!"
Spacious 2BR 2BA Condo & 2x Parking, Minutes from Central Sq, MIT, Harvard.

Gorgeous Beacon Hills Studio next to State house

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay here. Room very clean and accommodations good. Nice area. Near State House and Park Street subway. "
The price is AU$397
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Beacon Hills Studio next to State house

Pet-Friendly Revere Getaway, Steps from the T!

10.0 out of 10, Exceptional, (37)
"Beautiful home with a short walk to the beach. This home is warm and welcoming. All the amenties you need. The owners are very responsive and have made the check-in process seemless. Revere Beach is beautiful and gives you easy access to everything Boston and beyond. We will definitely stay here again on our next visit! "
Pet-Friendly Revere Getaway, Steps from the T!

Spacious vacation townhome unit with a pool

10.0 out of 10, Exceptional, (10)
"Great owners. Great neighborhood, great property. The fresh eggs were awesome!"
Spacious vacation townhome unit with a pool

6 bedroom house in a quiet and convenient neighborhood

6.8 out of 10, (3)
"The good, Large House, lots of bedrooms. Felt very safe, nice Alarm system. And the Piano was very fun for a singing and having fun. Reconstruction in process. The bad, the beds, not good, the house is falling apart, scary stairs, the bath rooms are tiny and do not offer shampoo, conditioner, and conditioner. Could not find bath towels. The ugly - mouse droppings all over the kitchen. Mouse found in one bedroom, captured mouse and took outside. Let host know that there was a mouse and mice...
6 bedroom house in a quiet and convenient neighborhood

Spacious 4BR with Modern Amenities – Family-Friendly

7.6 out of 10, Good, (4)
"The location is just right. You’re away from the city and only about 20-45 minutes from main attractions. A lot of people complain about the traffic. I’m from Chicago. Traffic in Boston is a walk in the park. The home is beautiful. Well equipped with amenities, toiletries, plates, etc. there’s really nothing you would need to make your stay enjoyable, that this home does not provide. We were a party of 6. And ALL had ample room and space. The only reason why I’m not giving it a 5 star rating...
Spacious 4BR with Modern Amenities – Family-Friendly

Enchanting Hidden Door Escape

2.0 star property
9.8 out of 10, Exceptional, (7)
"We had a wonderful stay! It was a beautiful property that fit exactly what we needed it to! The table was a perfect place for card games and everyone to gather around!"
The price is AU$995
includes taxes & fees
9 Dec - 10 Dec
Enchanting Hidden Door Escape

Boston's Most Charming Bed & Breakfast - Heart of the City

9.6 out of 10, Exceptional, (113)
"We had a fabulous time staying in this lovely brownstone. The location was perfect, responsiveness from the host was perfect, and so were the amenities, layout, and accessibility. We would definitely return again."
Boston's Most Charming Bed & Breakfast - Heart of the City

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (43)
"I stayed here with family members. We thought the property was very lovely and in a pleasant neighborhood. Everything we could need was in the house. We especially appreciated the toiletries and the Nespresso provided. Kitchen was fully functional. The property was very clean and the bedrooms and living spaces were nicely decorated. It felt more personable and comfortable than staying in a hotel. It was truly a nice getaway for us who were in the area to explore Boston!"
Boston's Best Vacation Home
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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Other property types in Westwood

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very good, (493)
"We enjoyed our stay. It was walkable to Chinatown. Very accessible to subway station. We liked that our room was on the top floor. "
The price is AU$430
includes taxes & fees
1 Dec - 2 Dec
Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (152)
"Everything good "
The price is AU$349
includes taxes & fees
22 Dec - 23 Dec
Maverick Suites at 28 Fenway

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (951)
"Well managed and maintained. Clean and convenient. Breakfast of some sort would have been nice."
The price is AU$290
includes taxes & fees
2 Dec - 3 Dec
Crescent Suites Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.