Holiday rentals in Westwood

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Top-rated holiday rentals in Westwood

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Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

9–16 Sep

$171 SGD per night

Guest favourite

Guest suite in Sharon

4.97 out of 5 average rating, 145 reviews

Cozy Lakeview Guesthouse

This Lakeview Guesthouse is private and stunning! It has its private entrance, deck, and parking. It features 1 bedroom with a Queen Bed, TV, with a sliding door that opens to a deck. The living room has a view of the Lake and a smart TV. The bathroom includes a tub (not a jacuzzi) and sitting on bench shower. The kitchen is fully equipped with stainless steel appliances. Guests have access to the lake, via beach pass during the summer. During the winter you can skate at your own risk.

13–20 Oct

$251 SGD per night

Guest favourite

Home in Framingham

4.96 out of 5 average rating, 130 reviews

2BR—Charming 1900s Home—1st Floor—25min to Boston

Welcome to our Charming 1900s House! 1st Floor 1200sqft Private Rental @ our 3 Rental Property Sleeps 4 Adults/2 Children Features: Kitchen w/ Dishwasher + Essentials & Cookware Bathroom w/ Tub & Shower 2 Queen Bedrooms w/ Memory Foam Mattresses 1 Queen Memory Foam Sofa-Bed 3 Desks & Chairs Private Entrance Driveway Parking Laundry Room in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Playground/Park/Tennis Cleaned & Sanitized / COVID Conscious

1–8 May

$199 SGD per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 264 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

18–25 Nov

$130 SGD per night

Guest favourite

Guest suite in Wellesley

4.98 out of 5 average rating, 211 reviews

Spacious Private Entrance Master Bedroom/Bath

Private entrance master bedroom w/exclusive use of attached master bathroom. Studio apartment-like room w/private exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, stores, Whole Foods. Short drive to Babson. Sizable room, tasteful decor, king bed, sitting area, microwave, fridge (no TV). High-speed wifi, deck, situated amongst the treetops. Safe suburban neighborhood. Walk/jog trails, tennis courts, walk to spa/gym/yoga w/reasonable day fees.

8–15 Feb

$208 SGD per night

Guest favourite

Flat in Dedham

4.95 out of 5 average rating, 154 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

2–9 Jul

$307 SGD per night

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 182 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-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. 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, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

4–11 Mar

$203 SGD per night

Guest favourite

Home in Dedham

4.98 out of 5 average rating, 182 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home, just 1.5 miles from Boston's transit. 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. Pets and families are warmly welcomed.

29 Nov – 6 Dec

$469 SGD per night

Guest favourite

Flat in Randolph

4.88 out of 5 average rating, 283 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

12–19 Apr

$179 SGD per night

Guest favourite

Guest house in Framingham

4.97 out of 5 average rating, 199 reviews

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.

7–14 Feb

$151 SGD per night

Guest favourite

Flat in Natick

4.98 out of 5 average rating, 332 reviews

Scandi-Modern Apartment

Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles. EV charging available.

6–13 Oct

$173 SGD per night

Guest favourite

Loft in Natick

4.99 out of 5 average rating, 174 reviews

Lakeside Studio Loft

Bright, open, private 900 sq foot loft space on Lake Cochituate. This is a mother-in-law suite attached to our lakeside home. This airy studio includes a queen bed, kitchen (no stove or oven) toaster,microwave,hot plate and George Foreman grill, skylit bathroom, living room with television and lakeview deck.

15–22 Mar

$202 SGD per night