
House holiday rentals in Westwood
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Top-rated house rentals in Westwood
Guests agree: these houses are highly rated for location, cleanliness and more.

The Red Door Carriage House
The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

The Nest | A peaceful retreat in the city
Unwind and relax on a quiet street in the heart of Somerville. With easy access to Harvard, MIT, Tufts, and Boston, this newly updated Victorian home is a perfect base to explore all that New England has to offer. You can also visit an abundance of local restaurants and coffeeshops within walking distance. During your stay, you will enjoy full use of a smart TV, comfortable work-from-home setup, brand new washer/dryer/dishwasher/range, off-street parking, and multizone heating/ cooling systems.

Modern home 22 min Boston, 20 min Gillette Stadium
Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and unlimited on-street parking. Pet friendly!

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN
Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

Cozy house close to Boston
My home is very comfortable with a casual feel. I have three bedrooms with 1.5 bathrooms. I have two queen size beds and one twin size bed. My kitchen and bathrooms are updated. I have a cozy den with a Smart TV and a living room that is a comfortable place to relax. The outdoor area has a deck leading onto a patio with a fire pit. I have an outdoor gas grill. It's a great place to unwind and relax. It is fenced in with privacy. I also have a driveway and on street parking is available.

Cozy en suite w/ high ceilings
 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

1BR Loft | 25 Mins to Boston | Quiet Neighborhood
Welcome to The Loft! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Mattress Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Essentials Dining Area — Table & Chairs Living Room — Leather Sofa 49" SmartTV — Netflix + Sling Live TV Bathroom — Shower, Plush Towels & Natural Bath Products Private 2nd Floor Entrance Heated Outdoor Stairs ASAP Snow Removal/Car Cleared Off Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized Easy Access —Route 9 & 90-Mass Pike

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt
This is a 1st floor private unit nestled in a serene urban enclave. Conveniently surrounded by public transit, shops, and dining options within a 0.6-mile radius. Originally a charming Victorian abode, meticulously renovated in 2016 to seamlessly blend historic elegance with contemporary comforts. Revel in a fully-equipped kitchen, private rear porch, and a tranquil bedroom boasting a plush queen-size bed. Tailored for your short or extended stay needs, with central air for optimal comfort.

Entire Apartment in Stoneham
Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

Quaint 3 bedroom home in Cohasset Village
You will love staying in this quintessential coastal town. Newly updated village colonial in walking distance to town restaurants, the common and harbor. This is a quaint single family home offers full kitchen, brand new bathroom, primary bedroom with a queen bed, makeup area and a small walk in closet The 2nd bedroom also has a queen bed and the third bedroom has a twin bed. There is a large living room, dining, front porch, and a very large deck/backyard and a great neighborhood.

Treetop Haven in the City
This is a sweet, cozy space that is not fancy but homey. You will have everything you need for a comfortable stay including a complete kitchen with everything you will need to make your own meals. We are conveniently located, near the subway and buses, supermarkets, restaurants, and coffee shops. We are within two blocks of the jewel of the Emerald Necklace, Jamaica Pond, and other green spaces. Read our reviews so you can see what previous guests have loved about Treetop Haven.

Cozy, historic 3 bedroom home close to Boston!
Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.
Popular amenities for house rentals in Westwood
House rentals with a pool

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

Cozy Barrington Home with a Private Pool

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Spacious vacation unit in premium suburban town

Seaview Summit | Ocean Views, Indoor Pool, Beach

Nature's Nook

Large groups. Private Retreat. Entire home
Weekly house rentals

Elegant Guest suite Wellesley

New modern 2bd condo: free parking/near train

The Cozy Colonial - 4 BDRM house with parking

Renovated Cozy City Getaway

Beautiful home next to train to Boston, near Salem

Cozy Home next to City Park

New Spacious Home in Boston

Quiet 1BR • Wi-Fi • Parking Included • In Randolph
Private house rentals

Rent the Beach at Lakeshore Retreat

Charming Boston Single Fam Home Near Commuter Rail

Woodland View

Upscale Boston 2 BR w/ Off Street Parking

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

Stylish Retreat in Historic Quincy | Pet Friendly

Elegant 4BR Retreat | Yard & Parking | Dedham

Relaxing Waterfront Lake House, 10 min to Gillette
When is the best time to visit Westwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £57 | £59 | £57 | £60 | £67 | £75 | £67 | £69 | £71 | £81 | £75 | £71 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Quick stats about house rentals in Westwood

Total holiday rentals
Explore 30 holiday rentals in Westwood

Nightly prices starting at
Westwood holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 2,200 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Westwood holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Westwood rentals

4.9 Average rating
Westwood stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Freedom Trail
- New England Aquarium
- Boston Seaport
- MIT Museum
- Boston Convention and Exhibition Center
- Canobie Lake Park
- Crane Beach
- Gillette Stadium
- Duxbury Beach
- Museum of Fine Arts
- Quincy Market
- Onset Beach
- Prudential Center
- Roxbury Crossing Station
- Roger Williams Park Zoo
- Boston Children's Museum
- Symphony Hall




