
Holiday houses in Westwood
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Top-rated holiday rentals in Westwood
Guests agree: these stays are highly rated for location, cleanliness and more.

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)

Modern Somerville Cottage
My place is a beautiful new house located in the Hip neighborhood of Davis Sq in Somerville. Conveniently on the bike bath leading to Davis Sq with its T stop and all its great restaurants and bars (15 min walk). 2 Mins walk to the new Green line extension that takes you to Cambridge and Boston. Modern furnishings throughout with amazing light from all sides and double height cathedral ceilings in the living/dinning room. I also have 2 beautiful condos in Killington VT please ask for info

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.

Country Charm minutes from the Hub - 1st Floor Apt
Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

~*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

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!

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!

Conveniently Located Private Garden Apartment
Garden-level apartment next to a public park yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy to take in all the 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.

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.

Private guest house on beautiful country road
Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

Windy Knob Farm Cottage - stay on a working farm
A former caretaker's cottage located on a 92-acre historic farm just 40 minutes from Boston. Home to abundant wildlife and farm animals, spectacular sunsets, lush pastures, rolling hills and meadows, woodlands, a pond and bogs. Walking trails nearby on property, and farmstand produce/eggs are produced onsite. Come stay to enjoy a change of scenery!

Historic JP Brownstone with Parking. Pets Welcome!
Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).
Popular amenities for Westwood holiday rentals
Other great holiday rentals in Westwood

Family Vacation Modern Home

Steps to the Green Line & Minutes from Boston! #28

Cozy studio near-Train&Bus, W/Parking in Boston

Conveniently Located & Comfy Suite FIFA World Cup!

1BrApt FreeParking 6minT/Subwy FullKitchn WashDryr

Quiet 1BR • Wi-Fi • Parking Included • In Randolph

Cozy Guesthouse Near T-Station - Family Friendly

Family Paradise/20 min from Gillette Stadium
When is the best time to visit Westwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $158 AUD | $155 AUD | $149 AUD | $171 AUD | $176 AUD | $186 AUD | $179 AUD | $201 AUD | $171 AUD | $185 AUD | $194 AUD | $158 AUD |
| 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
Do house rentals in Westwood have wifi?
Absolutely! We offer over 30 house 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 house rentals in Westwood have a kitchen?
Absolutely! We offer over 20 house 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 310 vacation rentals in Ashcroft, over 340 vacation rentals in Greenlodge, and over 310 vacation rentals in East Dedham.
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 a kitchen, over 10 homes with wifi, 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 70 holiday rentals in Westwood

Nightly prices starting at
Westwood holiday rentals start at $45 AUD per night before taxes and fees

Verified guest reviews
Over 5,140 verified reviews to help you choose

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

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Westwood holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- TD Garden
- Fenway Park
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- New England Aquarium
- MIT Museum
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Massachusetts Institute of Technology
- Museum of Fine Arts
- Quincy Market
- Onset Beach
- Prudential Center
- Roger Williams Park Zoo
- Boston Children's Museum
- Roxbury Crossing Station
- Salem Willows Park
- Franklin Park Zoo
- Bunker Hill Monument
- Symphony Hall




