Holiday rentals in Westwood

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Top-rated holiday rentals in Westwood

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Top guest favourite

Guest suite in Weston

4.99 out of 5 average rating, 164 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, 266 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

4.89 out of 5 average rating, 76 reviews

Conveniently Located & Comfy Suite - Summer's Best

Welcome to your perfect retreat whether you are traveling for business, leisure or just want a family gateway! The entire first floor of the house is yours to enjoy. The place has a furnished bedroom, full bathroom, kitchen, gaming area offering you the most comfort and privacy you desire. With onsite parking and a private entrance, you'll have everything you need right at your fingertips. Take advantage of close by restaurants, bars, stores or try TopGolf, movie theater and bowling alley.

Superhost

Flat in Dedham

4.84 out of 5 average rating, 190 reviews

Lovely townhouse apartment minutes from Boston

Book your stay at this peaceful and centrally-located townhouse-style apartment just minutes from Boston. This newly renovated space features 2 bedrooms (one queen bed and one twin bed), one full bath (second floor), cozy living room with pull out sofa, and eat-in kitchen. Take advantage and relax by the outdoor fire pit (reservations required) or walk to Dedham Square for delicious food and shopping. Dates you need not available? Make sure to check out our other listing just next door!

Top guest favourite

Serviced apartment in Dedham

4.96 out of 5 average rating, 196 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, 298 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!

Superhost

Flat in Norwood

4.76 out of 5 average rating, 55 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. 10 min walk to train station . Franklin train takes 25 min to S. Station in Boston, or 30-40 min drive. Private, furnished, 1 bed., 1st fl. apt. , quiet, clean, well lit. Full kitchen . . NO onsite laundry. Laundromat close by. On site parking for ONE car only. No smoking, pets, parties, or gatherings. Quiet time after 10pm

Guest favourite

Guest suite in Westwood

4.79 out of 5 average rating, 75 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.

Guest favourite

Guest suite in Lexington

4.97 out of 5 average rating, 128 reviews

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

Top guest favourite

Guest suite in Wellesley

4.97 out of 5 average rating, 290 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.

Top guest favourite

Home in Dedham

4.98 out of 5 average rating, 245 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.

Top guest favourite

Guest house in West Roxbury

4.95 out of 5 average rating, 197 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.