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

94_Elegant 4BR Home w/Yard & Ample Parking, Dedham
Welcome to your elegant Dedham retreat! This fully renovated 4BR/3BA home blends modern design with comfort, featuring an open living and dining area, a fully equipped kitchen, and beautifully styled bedrooms. Enjoy a private fenced yard, four parking spots, and in-home laundry. Just a 10-minute walk to the subway for easy access to downtown Boston, and about 18 minutes to Gillette Stadium depending on traffic. We’d be delighted to host you book now and experience comfort with a touch of luxury!

Spacious Suite 8 mi from Gillette Stadium
Come stay with us for the 2026 World Cup! This spacious two bedroom one full bath guest unit is all yours to enjoy and call home for your visit. This unit has parking for 1-2 cars and a washer/dryer. The house is nestled behind an old mansion. It is close to markets and the center of town. The Commuter Rail makes 2 stops in town and will take you into Boston in minimum a ½ hour. The World Cup at Gillette Stadium, Home of The New England Patriots, and the popular Shopping Center is 8 miles away.

Great hotel alternative.Close to Boston
Adults only. Best for one, doable for 2 persons. Two person max. location. 10 min walk to town center. Plenty of shops/restaurants. 12 miles to Boston. Train station (Franklin line) very close. 25 min to S. Station in Boston, or 30-40 min drive. Private, fully furnished, 1 bed., 1st fl. apt. , quiet, clean, Full kitchen . . NO onsite laundry. Laundromat close by. Heat controlled by landlord. On site parking for ONE car only. No smoking, pets, parties, or gatherings. Quiet time after 10

Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Entire Historic Carriage House with Fireplace & AC
Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

A King Bed | Apartment | Middle of Boston
Located in the geographical middle of Boston you can get to anywhere in the city within 20 minutes including Harvard/MIT, Downtown, Fenway, Hynes Convention Center, Seaport and more. This pseudo apartment on the first floor is separate from the rest of the house and has its own private entrance, a private bathroom and a dedicated off street parking spot. The full kitchen with oversized counter is great for eating; comfy living room for relaxing and an office nook for working.

the house of id; vintage shop, accessible space
🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

5 min walk to T train, 20 min to Downtown Boston
Beautiful newly renovated one-bedroom guest suite with ~600 sf living space. Private entrance in a quiet neighborhood. Contactless check-in. Plenty of parking. Minutes walk to the T train station (128/University Station), then 20 minutes to downtown Boston. Walk to shopping (Wegmans, Target, HomeGoods, etc.) and restaurants. Easy access to highway I-95. No smoking anywhere on-site. Quiet hour: 10pm-7am Host approval needed for visitor beyond registered guest.

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.

Private guest house on beautiful country road
Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

The Plant Haus
A peaceful oasis with easy access to Rt 1, Rt 128, and walking distance from Norwood Center and the Norwood Depot commuter rail stop that goes to South Station. 30 mins from Providence and Boston and less than 20 mins to Gillette Stadium. My place is located in a quiet community. I am just a phone call or text away should you need me!

Private apartment close the city!
New couch! New towels and linens! Fresh paint! New flooring coming soon. This private apartment is part of my home but has a separate entrance, full bath, living room and private bedroom. We're in a family neighborhood close to the city, and very convenient for those visiting with a car.
Popular amenities for Westwood holiday rentals
Other great holiday rentals in Westwood

Boston Charm 5: Private Room Near Downtown

Historic Federal Period Bedroom Suite

CLEAN, SPACIOUS & MODERN 🌟 relax & feel at home!

Cozy furnished room w private bathroom

Private room #2 in Westwood MA

[Blissful Room 8 min Harvard Sq]

private room w/ 2 bed pet friendly

Cozy Somerville Room (Near MBTA/Bike Path)
When is the best time to visit Westwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $137 SGD | $134 SGD | $129 SGD | $148 SGD | $152 SGD | $161 SGD | $155 SGD | $174 SGD | $148 SGD | $160 SGD | $167 SGD | $137 SGD |
| 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 |
Frequently Asked Questions
Do house rentals in Westwood have wifi?
Absolutely! We offer over 30 house rentals with wifi in Westwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Westwood?
Experience the best of Westwood with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Westwood have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Westwood. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Westwood?
Yes! Work meets play with ease at over 40 vacation rentals in Westwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Westwood have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Westwood. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Westwood?
Make yourself at home in Westwood by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Ashcroft, over 340 vacation rentals in Greenlodge, and over 310 vacation rentals in East Dedham.
Are there family-friendly vacation rentals in Westwood?
Westwood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Westwood?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Westwood?
Four-legged friends are welcome in Westwood. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Westwood have free parking?
Absolutely! We offer over 30 house rentals with free parking in Westwood. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Westwood

Total holiday rentals
Explore 60 holiday rentals in Westwood

Nightly prices starting at
Westwood holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 3,770 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 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!
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- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- MIT Museum
- New England Aquarium
- Freedom Trail
- Good Harbor Beach
- Canobie Lake Park
- Duxbury Beach
- Crane Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Onset Beach
- Prudential Center
- Oakland Beach
- White Horse Beach
- Roger Williams Park Zoo
- Franklin Park Zoo
- Salem Willows Park
- Symphony Hall




