
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.

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)

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 15-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.

Lovely 2 bedroom apartment minutes from Boston
Book your stay at this peaceful and townhouse-style apartment just minutes from Boston. This renovated space features 2 bedrooms (one queen bed and one full bed), one full bath with glass shower (second floor), living room with pull out sofa, and eat-in kitchen with designated work space. Take advantage and relax by the outdoor fire pit (reservations required) or walk to Dedham Square for food and shopping. Dates you need not available? Make sure to check out our other listing next door!

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.

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!

Modern 1BR apt in Boston’s Roslindale Village
This place is on the 3rd floor of our newly renovated home in Boston's Roslindale, which is about 6 miles away from downtown (please look up the neighborhood to have a clear idea where it is). Our place is close to restaurants & bars in Rozzy Village and West Roxbury. There is a connection via bus at the corner to the subway at the Forest Hills Orange Line T-stop that will get you to downtown in about 30 min, and there is commuter rail in Roslindale Village.

Comfortable apartment in Framingham
Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

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.

3 bedroom impeccable private home, quiet street
Clean, quiet house with 3 bedrooms, full kitchen, fenced in yard, smart TVs (no cable). Quiet, safe, clean neighborhood, close to restaurants, and amazing outdoor destinations (Blue Hills reservation for hiking, swimming, photography, biking, etc), also golf course, horse barns, rock climbing, ice rink and more! Please note, the driveway and yard are shared with the downstairs unit.

Country Cottage in the City
This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.
Popular amenities for Westwood vacation rentals
Other great vacation rentals in Westwood

Elegant Guest suite Wellesley

⭐️Perfect for business travelers & college visits⭐️

Spacious Suite 15 mi from Boston

Comfortable Boston Bedroom 03

Cozy 2-Bedroom Apartment Near Dedham Legacy

#214-D Easy Commute and Mature Trees

Top Boston Suburn/Lake & Nature Family Retreat

Newly renovated cozy apartment!
Quick stats about vacation rentals in Westwood
Total rentals
60 properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Frequently Asked Questions
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.
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.
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.
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 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.
Where should I stay in Westwood?
Make yourself at home in Westwood by choosing from our most frequently booked neighborhoods. We have over 290 vacation rentals in East Dedham, over 290 vacation rentals in Ashcroft, and over 320 vacation rentals in Greenlodge.
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 wifi, over 10 homes with a kitchen, 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.
Destinations to explore
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