Holiday houses in Weston

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Top-rated holiday rentals in Weston

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Top Guest favourite

Home in Wellesley

5 out of 5 average rating, 40 reviews

Elegant Guest suite Wellesley

Enjoy a stylish experience at this centrally-located guest suite (attached to owners's main house), 5 min drive to Babson & Wellesley College. 15 mins walk to Linden Square /Whole Foods. Private smart access. Huge Backyard/Garden. Patio, fast WiFi, 1 covered garage, central AC /Heating with separate zone. 1 BR with Queen size bed, kingsize sofa bed and working station plus walk-in closet with washer & dryer. 2 full Bathrooms. Living room, smart TV, dinning table and full functioning kitchenette.

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 Waltham

4.84 out of 5 average rating, 61 reviews

2bed/2bath Apt at Waltham Landing - Apt 306

This apartment complex was built in 2016. It is 1 block from The Charles River and Waltham's famous Moody Street, aka "Restaurant Row." Across the street from Waltham Station: Fitchburg Line - Commuter Rail. Bentley and Brandeis are 1 mile away. Monthly rentals accepted (inquire for best rate), discounts for groups and long-term rentals. Perfect for business travelers, families, anyone in between housing or visiting town! Free parking in the parking lot. Yes there is an Elevator.

Guest favourite

Home in Weston

4.97 out of 5 average rating, 94 reviews

Spacious vacation unit in premium suburban town

Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2K Sqft of space. There are chickens in the backyard...the host can provide some fresh eggs too if desired.

Superhost

Guest suite in Wayland

4.88 out of 5 average rating, 150 reviews

Spacious Two Bedroom Apartment

Private and clean renovated 2 bedroom apartment in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 6 comfortably in 2 queen beds and 1 futon. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27. Close to many colleges and MetroWest office parks.

Top Guest favourite

Guest suite in Wellesley

4.97 out of 5 average rating, 286 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 West Newton

4.92 out of 5 average rating, 228 reviews

Private 1 Bedroom suite In West Newton

Separate & private entrance to the lower level of a single-family home. You will have a clean, quiet bedroom, sitting area & private bathroom all to yourself. There is off street parking. There is a fridge/microwave. Newton is 10 miles west of Boston and easily accessible by public transportation & the MA Pike, Rt 95 & 128. The neighborhood is very quiet and safe. I follow all the AirB&B cleaning protocols.

Guest favourite

Guest suite in Waltham

4.96 out of 5 average rating, 25 reviews

Cozy & convenient place with sunset & garden view

Clean, quiet, and airy private suite in a safe and quiet neighborhood in Waltham. You’ll find almost all amenities just like home. A few mins away from shopping malls, great restaurants, groceries in Moody st., and booming biotech hub in Waltham, and all major highways. 15-20mins to downtown Boston and airport. Scroll down for my guidebook and personal favorites. Reach out if you have any questions

Guest favourite

Guest suite in Wellesley

4.81 out of 5 average rating, 311 reviews

Private suite 1 BR, 1 BA, 1 LR, 1FLR

Prime location in Wellesley Hills, MA. Garden level suite offers a living room and a bedroom with a private bath. It offers a full size bed in the bedroom and a queen size pullout sofa in the living room. Private entrance with smart lock entry. Easy access to commuter rail, restaurants, post office, bank, Babson College, Wellesley College and Olin College of Engineering and so much more.

Top Guest favourite

Home in Framingham

4.94 out of 5 average rating, 53 reviews

Cozy en suite w/ high ceilings

Enjoy this peaceful oasis with backyard views of the tall pine forest and soothing sounds of a patio waterfall. Private entrance en suite features off street parking, air conditioning, easy access to major amenities. 10 minutes to Mass Pike. 5 minutes to Framingham State University. Very safe and easily walkable neighborhood. Use of propane fire pit upon request.

Top Guest favourite

Guesthouse in Framingham

4.97 out of 5 average rating, 282 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.

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Other great holiday rentals in Weston

Guest favourite

Private room in Newton

4.89 out of 5 average rating, 57 reviews

Room w/private bathroom, private entrance, Newton

NikitaRating, 5 stars2 weeks ago

The house is beautiful and cozy, just like the photos. The host was incredibly kind, helpful, and quick to respond. Absolutely loved staying here — highly recommended!

Guest favourite

Private room in West Newton

4.88 out of 5 average rating, 25 reviews

Spacious guest Suite W/Private Full Bath @Newton

KylieRating, 5 stars1 week ago

This was a great fit for us as we were helping our daughter move in the area and needed to be close. The room was exactly as described and spotless. Sophie was extremely nice and flexible upon check-in. We worked from the room during the day so the desk with a monitor was a massive perk, as were the adorable chipmunks we could watch from the window. My only reservation would be if you like to sleep in, it can be a tad noisy with hustle and bustle above (two adorable boys). You can not beat the location, definitely recommend!

Guest favourite

Private room in Newton

4.87 out of 5 average rating, 187 reviews

Lovely room close to Boston with parking

TaichengRating, 5 stars1 week ago

Great location! Convenient walk from commuter rail station. Good quiet spot. The host has impeccable taste in art!

Top Guest favourite

Private room in Newton

5 out of 5 average rating, 53 reviews

Perfect Metro Boston Sunny Room - Newton/Wellesley

KarenRating, 5 stars7 months ago

My mom stayed at Danila’s place and she had a wonderful experience. My mom doesn’t speak English and Danila really tried to communicate with her and helped her. The house is beautiful and very clean. I can’t think about a better place where my mom could have stayed. I highly recommend it!

Top Guest favourite

Private room in Wellesley

4.97 out of 5 average rating, 97 reviews

Private room with a view

EmmaRating, 5 stars3 weeks ago

Morse House is a very clean,comfortable and peaceful place to stay. Marilyn is always very attentive to any request,always adding her personal and warm touch.She is very professional. I’ve been there more than 4 times in the last 3 years and it is always my choice # 1. I’ll be forever grateful.

Top Guest favourite

Private room in Arlington

4.93 out of 5 average rating, 320 reviews

Arlington Craftsman Green Room, Int. Well Restored

RishabhRating, 5 stars6 days ago

Thomas is an exceptional host and this place is absolutely amazing! The house has a beautiful aesthetic and a calming vibe, and it was spotless and very well-managed. I especially loved how the room was organized, it had a romantic charm to it that really stood out. The furniture was top notch and honestly the place looks so much better in person than in photos (which is rare!). This was actually my first Airbnb stay in the States and I ended up being an hour late for checkout. Thomas was incredibly kind and didn’t even charge me for the delay, such a thoughtful gesture. The neighborhood is quiet, peaceful, and just adds to the overall experience. I would highly recommend this place to everyone, and I’ll say it again, it’s ten times better in person! Thank you Thomas for your hospitality, will surely keep coming back to your place frequently hereafter! Hahaha

Superhost

Private room in Waltham

4.87 out of 5 average rating, 61 reviews

Best location in Waltham MA, room #2

NerissaRating, 5 stars7 months ago

It was a wonderful stay in a quiet neighborhood. Very close to Prospect Hill Park which had amazing reviews. I got the Charlie ticket pass and was able to navigate public transit to easily get downtown. Carlos was very friendly. He had lots of cool stories to tell. He gave me quite a few recommendations about what to see as well. Also, he was kind enough to give me a ride back to the airport so I wouldn't have to worry about being on bus and train with my luggage. It was also really cool staying in a building that was built in 1895.

Guest favourite