Holiday rentals in Weston

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Top-rated holiday rentals in Weston

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Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 102 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

12–19 Mar

$137 SGD per night

Guest favourite

Flat in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You will love this large 400 sq. ft private 1 bedroom studio. This unit has a private entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

13–20 Mar

$170 SGD per night

Guest favourite

Guest suite in Weston

5.0 out of 5 average rating, 115 reviews

FLOWER FARM GETAWAY 2BR 15MIN TO BOSTON

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 15 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.

13–20 Dec

$306 SGD per night

Superhost

Flat in Newton

4.85 out of 5 average rating, 123 reviews

Entire Apartment in Newton, Close to Boston!

Come stay in this comfortable one bedroom apartment with large open space living room, kitchen area, bathroom, Wi-Fi, parking, and a private entrance onto a gorgeous backyard garden. Centrally located in a quiet neighborhood equidistant from Moody St. in Waltham and West Newton Sq. -- a 15 minute walk from excellent restaurants and an independent movie theater in both directions. Two dance studios with regular weekend dances nearby. To protect guests with allergies, no pets allowed.

19–26 Sep

$180 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

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.

5–12 Mar

$203 SGD per night

Guest favourite

Flat in Maynard

4.91 out of 5 average rating, 441 reviews

New Renovated Attic Apartment in Downtown Maynard

Newly renovated private attic apartment in downtown Maynard with full kitchen, living room and bedroom/office. A warm, cozy space with plenty of natural light! Free parking on site for 1 vehicle, and only 2 miles from the Fitchburg commuter rail line, which will bring you right into North Station in Boston! Walking distance to restaurants, cleaners, movie theater, gym, golf course, shopping... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

24 Jun – 1 Jul

$188 SGD per night

Guest favourite

Townhouse in Concord

4.93 out of 5 average rating, 330 reviews

Cottage Suite-Walk to Shops, Train. Town approved.

This is a private unit with no shared areas. It is the front corner of our house and is completely separate. However, you will share walls like in an apartment. Kitchen includes: sink, microwave, fridge, Keurig, and water boiler. Private gated outside lawn and patio. History, nature, dining & shopping are VERY CLOSE. Open and welcoming to ALL types of people. There is a CLEANING FEE in addition to the nightly fee. TV with internet (Prime, Hulu & Netflix) but NO LIVE TV OR CABLE

15–22 Jun

$253 SGD per night

Guest favourite

Flat in Hudson

4.85 out of 5 average rating, 292 reviews

Private Mother-In-Law apartment on the lake!

Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

18–25 Sep

$119 SGD per night

Guest favourite

Flat in Newton

4.96 out of 5 average rating, 381 reviews

Sunny apartment in gracious Victorian

Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

6–13 Jul

$227 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.

23–30 Mar

$158 SGD per night

Guest favourite

Guest suite in Arlington

4.92 out of 5 average rating, 196 reviews

Modern and comfortable studio apartment

Cozy modern walk-in studio apartment with on-site parking. Located in the Captain Wyman-Pichette House dating from 1840, across from Spy Pond and in Arlington's Historic Pleasant Street district. Steps from public transit to downtown Boston, a short walk to Arlington Center shops, great restaurants and Minuteman Bike Trail. Access to garden patio.

3–10 Nov

$147 SGD per night