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

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

3 bdrm 2 bath home Walk to the Gillette Stadium
Welcome to a perfect getaway just 1 mile from Gillette Stadium! This updated 3-bedroom, 2-bath duplex home is ideal for Patriot games, Concerts, & weekend escapes. Walk to Gillette & avoid parking costs & traffic. Ask about early arrivals, featuring an oversized deck-gas fireplace, grill & firepit. On a quiet wooded acre, this home offers both convenience and relaxation. 1 hr to Beaches/ Mountains. Situated between Boston & Providence Major Events: - World Cup Soccer 2026 - Patriot games

Charming Townhouse in Historic Town near Boston.
Spacious freshly renovated townhouse, part of an antique two family house. Separate entrance, private parking space. One big bedroom with a very comfortable queen size bed and huge closet. Living room has a queen size sofa sleeper, new smart TV, and two closets. Window a/c in the bedroom, window fan in the living room. Fully equipped eat-in kitchen. Brand new beautiful bathroom with a tub. For stays longer than 3 nights you can use washer and dryer that are located in the basement. (Not shared)

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 abundance on-street parking. Pet friendly!

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.

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod
Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Two bedrooms, full bathroom, and breakfast room
We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

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!

Inn at Newton Highlands, Suite 2, Apartment-Hotel
This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

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.

Windy Knob Farm Cottage - stay on a working farm
A former caretaker's cottage located on a 92-acre historic farm just 40 minutes from Boston. Home to abundant wildlife and farm animals, spectacular sunsets, lush pastures, rolling hills and meadows, woodlands, a pond and bogs. Walking trails nearby on property, and farmstand produce/eggs are produced onsite. Come stay to enjoy a change of scenery!
Popular amenities for Westwood holiday rentals
Other great holiday rentals in Westwood

Charming 3BDR Boston Stay Garage + EV + Pool Table

Elegant Guest suite Wellesley

Luxurious Victorian Carriage House

New modern 2bd condo: free parking/near train

Slow Down| Your Boston Getaway

Explore Boston in style! Dream home (STR-26-3)

On the Water Gem - 2 BR -The Cove Lanesville

Pelicans Bog on Woods Pond in Middleboro
When is the best time to visit Westwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 NZD | $177 NZD | $171 NZD | $196 NZD | $201 NZD | $213 NZD | $205 NZD | $230 NZD | $196 NZD | $225 NZD | $220 NZD | $218 NZD |
| 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
Are there family-friendly vacation rentals in Westwood?
Westwood has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Westwood?
Experience the best of Westwood with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
Are there vacation rentals with a dedicated workspace in Westwood?
Yes! Work meets play with ease at over 50 vacation rentals in Westwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Westwood?
Make yourself at home in Westwood by choosing from our most frequently booked neighborhoods. We have over 350 vacation rentals in Greenlodge, over 310 vacation rentals in Ashcroft, and over 310 vacation rentals in East Dedham.
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.
Do apartment rentals in Westwood have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Westwood. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Westwood have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Westwood. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Westwood have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Westwood. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Westwood?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with wifi, over 30 homes with a kitchen, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Westwood

Total holiday rentals
Explore 80 holiday rentals in Westwood

Nightly prices starting at
Westwood holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 4,830 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Westwood holiday rentals include Wi-Fi 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
- Harvard University
- Boston Common
- New England Aquarium
- Brown University
- Revere Beach
- Northeastern University
- Boston Seaport
- Boston University
- Freedom Trail
- MIT Museum
- Boston Convention and Exhibition Center
- Gillette Stadium
- Duxbury Beach
- Canobie Lake Park
- Crane Beach
- Quincy Market
- Museum of Fine Arts
- Onset Beach
- Roxbury Crossing Station
- Prudential Center
- Roger Williams Park Zoo
- Boston Children's Museum




