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.

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Top guest favourite
The kitchen features modern appliances and a central island with seating for five. Light-colored cabinetry and a mosaic tile backsplash complement the dark granite countertops. Pendant lights illuminate the workspace, while a large window brings in natural light.
Home in Holliston
4.98 out of 5 average rating, 128 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 favourite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton
4.94 out of 5 average rating, 146 reviews

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!

Top guest favourite
Home in Hyde Park
4.86 out of 5 average rating, 344 reviews

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

Top guest favourite
Guest suite in Weston
4.99 out of 5 average rating, 198 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 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top guest favourite
The exterior of a historic home is surrounded by tall trees, with a gentle slope of green lawn leading to the entrance. A spacious garage is visible on the right. The sky is painted in soft hues, indicating sunset.
Guest suite in Dover
4.97 out of 5 average rating, 318 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.

Guest favourite
Guest suite in Westwood
4.82 out of 5 average rating, 89 reviews

5 min walk to T train, 20 min to Downtown Boston

Beautiful newly renovated one-bedroom guest suite with ~600 sf living space. Private entrance in a quiet neighborhood. Contactless check-in. Plenty of parking. Minutes walk to the T train station (128/University Station), then 20 minutes to downtown Boston and 13 miles to Gillette Stadium. Walk to shopping (Wegmans, Target, HomeGoods, etc.) and restaurants. Easy access to highway I-95. No smoking anywhere on-site. Quiet hour: 10pm-7am Host approval needed for visitors beyond registered guest.

Top guest favourite
Guest suite in Sharon
4.95 out of 5 average rating, 219 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 favourite
The exterior of a red house is framed by a well-maintained garden comprising various flowers and greenery. The house features a welcoming entryway, a chimney, and a grassy area. Sunlight illuminates the scene, highlighting the vibrant colors of the surrounding landscape.
Flat in Dedham
4.94 out of 5 average rating, 214 reviews

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

Top guest favourite
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
4.98 out of 5 average rating, 347 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!

Top guest favourite
A garden-level entrance is highlighted by a set of concrete steps leading to a private entry with a vibrant purple door. Adjacent is a second door framed by glass panels, creating a welcoming transition to the apartment. The surrounding area features a circular stone pathway.
Flat in Newton
4.93 out of 5 average rating, 397 reviews

Conveniently Located Private Garden Apartment

Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

Top guest favourite
A dining area with a dark wooden table is set for four, featuring a colorful table runner. Natural light filters through windows adorned with light curtains, illuminating a cozy living room space beyond, furnished with a sectional couch, decorative pillows, and houseplants.
Guest suite in Newton
4.95 out of 5 average rating, 146 reviews

New Markdown! Lovely 3 Bedroom Unit with Garage

Planning your World Cup trip? Boston host of 7 World Cup matches. Enjoy the comfort of a fully equipped home perfect for watching every game This beautiful sunlit second floor unit with private garage has 3 bedrooms, full bathroom, splendid modern kitchen, gracious dining room, an elegant living room and a dedicated pleasant office room . Enjoy the shared backyard with a patio and playground for the kids. Registration: STR - 24 - 12

Guest favourite
Guest house in Westwood
4.96 out of 5 average rating, 45 reviews

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

Popular amenities for Westwood holiday rentals

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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 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 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 House Rentals in Westwood?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with a kitchen, over 40 homes with free parking, over 40 homes with wifi, 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 £22 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    70 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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