
Vacation rentals in Westwood
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Top-rated vacation 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.

Private & Remote, Enjoy Outdoors, Sleep in Luxury
Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Flower Farm Getaway 2BR, 20 Min To Boston
Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

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

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!

Zen Inspired Retreat with Private Forest Trails
Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Beautiful Studio - < 15 mins 2 downtown & Brown
Relax, work, and unwind in “The Treehouse,” our serene, light-filled studio apartment nestled among the trees. Perfectly located in historic Rumford, RI, it’s just 3 miles from Brown, RISD, and Johnson & Wales, and 5 miles from Providence College. Enjoy quick access to the East Side of Providence, Newport, and Little Compton beaches. Conveniently close to Amtrak, bus lines, and the airport, it’s an ideal spot for exploring New England or visiting area colleges.

SUNNY- Nordic-Inspired Flat. Intimate & Beautiful
A magazine-worthy Nordic-Scandinavian flat inside a stunning Victorian mansion on Providence's West End. Guests call it serene, stylish, and unlike anything they've stayed in before! Spotlessly clean, beautifully designed, steps from Federal Hill's best restaurants, and directly across from The Nitro Bar. Dedicated off-street parking included. Perfect for groups, families, couples, or work trips with everything you need at your door.

Private Suite•Gillette Stadium/Boston•BBQ•Parking
Enjoy a cozy and private garden-level suite with your own entrance, offering comfort, privacy, and conveniences. 18 min car ride/20 min train ride to Gillette Stadium 25 min train ride to downtown Boston 20 min train ride to Northeastern University 27 minutes car ride to Harvard University, 18 minutes to Brandeis University, 30 minutes to Northeastern University, 02 free parking Quiet, safe neighborhood in Westwood

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 Westwood vacation rentals
Other great vacation rentals in Westwood

Modern Comfort

Charles Chateau Guest House w/ King & Queen Beds

Guest suite on cranberry bog, 1 mile from beach

Spacious Suite in a Central Location

Hidden Gem near Boston w/ Private lake access

Spacious & Peaceful 2BR in Boston w/ Free Parking

The Fisher: City Access • Kitchen • Gym • W/D

Great hotel alternative.Close to Boston
When is the best time to visit Westwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $147 CAD | $183 CAD | $193 CAD | $160 CAD | $164 CAD | $174 CAD | $167 CAD | $188 CAD | $160 CAD | $183 CAD | $179 CAD | $178 CAD |
| 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 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 house rentals in Westwood have a kitchen?
Absolutely! We offer over 30 house 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 house rentals in Westwood have free parking?
Absolutely! We offer over 40 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 free parking, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Westwood

Total vacation rentals
Explore 80 vacation rentals in Westwood

Nightly prices starting at
Westwood vacation rentals start at $42 CAD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Westwood vacation 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
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Gillette Stadium
- Northeastern University
- Boston Convention and Exhibition Center
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Onset Beach
- Roxbury Crossing Station
- Quincy Market
- Museum of Fine Arts
- Prudential Center
- Roger Williams Park Zoo
- Good Harbor Beach





