Holiday houses in Westwood

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Top-rated holiday rentals in Westwood

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Top Guest favourite

Home in Stoughton

4.97 out of 5 average rating, 114 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 unlimited on-street parking. Pet friendly!

Top Guest favourite

Guest suite in Weston

4.99 out of 5 average rating, 161 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 favourite

Guest suite in Dover

4.97 out of 5 average rating, 261 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

Apartment in Dedham

4.79 out of 5 average rating, 127 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 favourite

Apartment in Dedham

4.96 out of 5 average rating, 195 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

Place to stay in Sherborn

4.97 out of 5 average rating, 297 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

Guest suite in Uxbridge

5 out of 5 average rating, 239 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Guest favourite

Guest suite in Roslindale

4.92 out of 5 average rating, 104 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.

Guest favourite

Apartment in Newton

4.92 out of 5 average rating, 343 reviews

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.

Top Guest favourite

Guest suite in Wellesley

4.97 out of 5 average rating, 287 reviews

Spacious Private Entrance Master Bedroom/Bath

Private entrance master bedroom w/exclusive use attached bathroom. Studio-like room; exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, grocery. Short drive to Babson. Sizable room, tasteful decor, king bed, sofa, microwave, mini-fridge (NO TV/NO KITCHEN). High-speed wifi, deck, view of treetops. Safe suburban neighborhood; good walk trails, walk to tennis/spa/gym/yoga w/reasonable day fees.

Guest favourite

Guest suite in Brookline

4.89 out of 5 average rating, 246 reviews

Brookline Home with a Garden

The 1 bedroom apartment is in the basement of our single family home. There is free parking. It is equipped with its own entrance, bathroom, kitchenette, porch, and garden. There is 1 queen bed in the bedroom and 1 full bed in the studio living area. ***No kids under the age of 12 allowed

Top Guest favourite

Guest suite in Newton

4.98 out of 5 average rating, 660 reviews

Spacious suite with private entrance, parking spot

Spacious suite on the third floor of a Victorian home. Private entrance. Off-street parking for one car. Short walk to Boston express bus and other bus lines to Fenway, downtown, Cambridge and other areas. Less than two miles from Boston College. Seven miles from the center of Boston.

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Other great holiday rentals in Westwood

Top Guest favourite

Townhouse in Norwood

5 out of 5 average rating, 11 reviews

Family Vacation Modern Home

HeatherRating, 5 stars2 weeks ago

Stayed at Sonnys place for a concert at Gillette with a bunch of friends. 15 mins down rt 1. Place was clean and had everything we needed. Great place with a larger group for any event in the area. Thanks again!

Superhost

Home in Westwood

4.84 out of 5 average rating, 85 reviews

sweet little house

WillRating, 5 stars1 month ago

This is a cute ADU within walking distance to the Route 128 station. The unit is very spacious and reasonably priced. Wuke graciously helped us out when we needed laundry detergent. We would stay here again. Only downside is that the ADU has a bit of an unfinished feel. The shower did not have a curtain, the bedroom skylight window was papered over, and there was command-strip residue leftover in a few places.

Guest favourite

Guest suite in Westwood

4.89 out of 5 average rating, 76 reviews

Conveniently Located & Comfy Suite Summer's Best

LeslieRating, 5 stars3 weeks ago

I stayed here with my partner and my cousin for my sisters wedding. Everything was awesome! Steve is very responsive and was direct and clear on anything we had questions about. The listing is for the bottom floor of the house with a very spacious living room/kitchen area. The bed was so comfortable! We were surprised we couldn’t open the doors to the outside but it’s not the end of the world lol. Amazingly beautiful neighborhood, I greatly recommend if you’re in the area and don’t want to stay at a hotel!

Top Guest favourite

Home in Norwood

4.95 out of 5 average rating, 44 reviews

the house of id; vintage shop, accessible space

JasonRating, 5 stars3 days ago

Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!

Top Guest favourite

Guesthouse in Norwood

5 out of 5 average rating, 14 reviews

Spacious Suite 15 mi from Boston

VanessaRating, 5 stars3 weeks ago

Mia’s place looks better than the pictures, very clean, communication was nice and smooth. Check out time is 10am instead of the 11am the app stills shows but she communicates everything in a time matter

Top Guest favourite

Home in Dedham

4.98 out of 5 average rating, 242 reviews

Cozy, historic 3 bedroom home close to Boston!

KaitlynRating, 5 stars2 weeks ago

We had a great stay—perfect for our quick family trip! The home was incredibly clean, cozy, and well-stocked with everything we needed, from a pack ’n play to extra towels, bed linens, and kitchen essentials. Marybeth was wonderful to communicate with and shared some great local dining recommendations. We were very happy with our accommodations and would absolutely stay again!

Guest favourite