
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.

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.

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!

Quiet country apartment in farmland setting.
Cozy studio located on 90 acres of private property that includes conservation woodland and fields, perfect for a challenging hike and wildlife viewing. Apartment has 1 queen bed with roll out cot and a full bathroom with shower and selection of towels. The fully equipped kitchen comes with a refrigerator, microwave, and the washer and dryer downstairs mean less packing. When not out and about exploring the countryside there is WiFi and a smart TV to keep you entertained.

Mink Cove Treehouse
A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

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.

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!
Popular amenities for Westwood holiday rentals
Other great holiday rentals in Westwood

Enchanted Willow Boston Storybook Stay 3BR Parking

Orchards retreat

New modern 2bd condo: free parking/near train

Lakeside Cottage

Charles Chateau Guest House w/ King & Queen Beds

Peaceful 2BR w/ 2-Car Parking by Gillette & Boston

Cozy Milton Stay | 2BR | near Blue Hills Ski 14/1

Quiet 1BR • Wi-Fi • Parking Included • In Randolph
When is the best time to visit Westwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $135 SGD | $133 SGD | $128 SGD | $147 SGD | $151 SGD | $159 SGD | $153 SGD | $172 SGD | $147 SGD | $168 SGD | $165 SGD | $163 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
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 40 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 340 vacation rentals in Greenlodge, over 310 vacation rentals in Ashcroft, and over 310 vacation rentals in East Dedham.
Do house rentals in Westwood have air conditioning?
Absolutely! We offer over 30 house 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 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.
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.
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.
Quick stats about holiday rentals in Westwood

Total holiday rentals
Explore 70 holiday rentals in Westwood

Nightly prices starting at
Westwood holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 5,140 verified reviews to help you choose

Family-friendly holiday rentals
30 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
- Harvard University
- Boston Common
- Brown University
- Revere Beach
- Northeastern University
- Boston Seaport
- Boston University
- Freedom Trail
- MIT Museum
- New England Aquarium
- 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




