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
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Flat in Ashmont
4.96 out of 5 average rating, 141 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand spanking new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There are two great restaurants nearby - Molinari’s and Tavolo, as well as a local coffee shop & a Dunkin just across the T Station.

Guest favourite
A welcoming living area features a comfortable leather sofa with decorative pillows, complemented by a cozy armchair. A small coffee table sits atop a patterned rug, while artwork adorns the walls, creating an inviting space. Natural light streams through a nearby window.
Flat in Norwood
4.8 out of 5 average rating, 66 reviews

Great hotel alternative.Close to Boston

Adults only. Best for one, doable for 2 persons. Two person max. location. 10 min walk to town center. Plenty of shops/restaurants. 12 miles to Boston. Train station (Franklin line) very close. 25 min to S. Station in Boston, or 30-40 min drive. Private, fully furnished, 1 bed., 1st fl. apt. , quiet, clean, Full kitchen . . NO onsite laundry. Laundromat close by. Heat controlled by landlord. On site parking for ONE car only. No smoking, pets, parties, or gatherings. Quiet time after 10

Top guest favourite
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, 302 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.

Top guest favourite
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, 211 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.

Superhost
The living room features a comfortable couch adorned with a soft throw blanket. A large piece of artwork hangs on the wall, showcasing a vibrant floral design. Two stylish glass tables are positioned in front of the couch, accompanied by a decorative rug.
Home in Hyde Park
4.9 out of 5 average rating, 359 reviews

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

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, 322 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
An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.
Home in Norwood
4.97 out of 5 average rating, 63 reviews

the house of id; vintage shop, accessible space

🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

Guest favourite
A spacious living area features large windows offering views of greenery. A comfortable queen bed is set against one wall, while a pullout sofa sits opposite. Light-colored curtains frame the windows, and a stylish lamp is placed beside a round table.
Guest suite in Roslindale
4.9 out of 5 average rating, 205 reviews

Cozy Renovated Suite w/Free St Parking near Train

Newly renovated in-law suite located in the charming Roslindale neighborhood of Boston. A short walk from West Roxbury Center, Roslindale Village's shops and restaurants, and Bellevue commuter rail stop which gets you to Back Bay in 15 mins (or 20 Min Uber/drive). Features include a private entrance kitchenette, bathroom, large quiet back yard with patio and fire pit (avail Apr-Oct). Perfect for weekend getaways, working/commuting to Boston, or visiting friends and family!

Guest favourite
A light-filled living area features a beige couch with decorative cushions. A dining table with wooden chairs is visible in the background, beside a large window. A television is positioned on an adjacent wooden unit, complementing the neutral wall tones and flooring.
Guest suite in Westwood
4.81 out of 5 average rating, 83 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. 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 visitor beyond registered guest.

Top guest favourite
Flat in Everett
5 out of 5 average rating, 6 reviews

Sterling 1BR at Everett | Pool & Gym

Enjoy contemporary comfort in this bright and inviting 1BR/1BA apartment in Everett. The home features a modern kitchen with stainless steel appliances, convenient in-unit laundry, and a naturally lit living space designed for relaxation. Make the most of the community’s outdoor courtyard pool, 24/7 fitness center, and cozy lounge areas with fire pits. Located minutes from Encore, Assembly Row, and key highways, it offers easy access to all of Greater Boston.

Top guest favourite
The exterior of the house is shown at dusk, featuring a two-story design with a mix of gray siding and white trim. Soft lighting highlights the entrance and landscaping along the front, while a large grassy area is visible in front of the home.
Townhouse in Norwood
4.97 out of 5 average rating, 32 reviews

Family Vacation Modern Home

Our home is in a quiet and family-friendly neighborhood, yet still offers easy access to the vibrant city as well as the surrounding natural beauty. Enjoy the many next door restaurant within waking distance : Texas Road house , Panera Bread, Five Guy Burger, McDonald. Taco Bell , Panda Express and chili's. Wapole Mall : Kohl’s, Old Navy. Barnes and Noble , Joann Ann Fabric, T-Mobile , Party City and Five Below, and Aldi.

Top guest favourite
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, 272 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.

Popular amenities for Westwood holiday rentals

When is the best time to visit Westwood?

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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 $40 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 apartment rentals in Westwood have air conditioning?

    Absolutely! We offer over 10 apartment 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 320 vacation rentals in Greenlodge, and over 290 vacation rentals in Ashcroft.

  • 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.

Quick stats about holiday rentals in Westwood

  • Total holiday rentals

    Explore 60 holiday rentals in Westwood

  • Nightly prices starting at

    Westwood holiday rentals start at ÂŁ30 per night before taxes and fees

  • Verified guest reviews

    Over 3,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 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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