Vacation rentals in Westwood

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Top-rated vacation rentals in Westwood

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Top guest favorite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.97 out of 5 average rating, 106 reviews

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.

Guest favorite
A view of a historic church with a tall steeple is framed by nearby houses, showcasing trees without leaves indicating the season. Power lines and street signs are visible, with blue skies overhead.
Townhouse in Dedham
4.77 out of 5 average rating, 231 reviews

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)

Top guest favorite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
4.99 out of 5 average rating, 175 reviews

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.

Top guest favorite
A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.
Guest suite in Dover
4.97 out of 5 average rating, 297 reviews

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.

Superhost
The living room features a dark upholstered sofa with decorative pillows. A small side table rests beside the sofa, topped with a vase of fresh flowers. Natural light filters through the window adorned with sheer curtains, and a wall mirror adds depth to the space.
Apartment in Dedham
4.77 out of 5 average rating, 146 reviews

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!

Top guest favorite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.97 out of 5 average rating, 205 reviews

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.

Top guest favorite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.97 out of 5 average rating, 314 reviews

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!

Guest favorite
A spacious bedroom is depicted, featuring a king-size bed dressed in crisp white bedding. Warm light emanates from two bedside lamps, illuminating simple wooden nightstands. Dark window shades frame the windows, contributing to a calm and restful environment.
Apartment in Roslindale
4.92 out of 5 average rating, 114 reviews

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.

Top guest favorite
A stylish wooden bed frame with a floral-patterned comforter and two pillows is featured in the sleeping area. A bedside table with a lamp stands next to the bed, and a wooden dresser is positioned nearby against the wall.
Apartment in Framingham
4.97 out of 5 average rating, 294 reviews

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

Top guest favorite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham
4.98 out of 5 average rating, 263 reviews

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.

Superhost
A tranquil bedroom features a spacious bed with floral-patterned bedding. Two nightstands with matching lamps are positioned on either side. Natural light filters through sheer curtains, complementing the soft wall color and enhancing the serene ambiance of the room.
Home in Canton
4.81 out of 5 average rating, 185 reviews

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.

Top guest favorite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 204 reviews

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

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.

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