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Holiday houses in Weston

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Top-rated holiday rentals in Weston

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Apartment in Waltham
4.97 out of 5 average rating, 388 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'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own 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)

Guest favourite
A spacious studio layout is featured, with a queen-sized bed covered in a plaid blanket against one wall. A black leather sofa with red accent pillows faces the bed. Light-colored walls and carpet create a bright atmosphere, with multiple doors leading to other areas.
Guest suite in Newtonville
4.77 out of 5 average rating, 165 reviews

Comfy Newton Guesthouse

Priced for solo travelers but perfect for 2! Cozy studio, private entrance. Fully furnished w/queen sized bed (memory foam mattress), dresser, a/c, washer/dryer, bathroom with shower stall, closet, high speed Wi-Fi, kitchenette with a small fridge/freezer, griddle, sink, microwave, kettle, toaster, and rice cooker. On-street parking throughout the year on our quiet one-way street, driveway in the winter. Please note that the ceilings are 7 ft tall and shorter in some areas. Cameras outside.

Top Guest favourite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
4.99 out of 5 average rating, 185 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 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top Guest favourite
The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Apartment in Newtonville
4.87 out of 5 average rating, 560 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Top Guest favourite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 103 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Top Guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 329 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!

Guest favourite
An open living space features a modern gray sofa paired with a dark green accent chair. A round coffee table sits on a textured blue rug. Natural light enters through large windows, illuminating the dining area and kitchen with stainless steel appliances and wooden cabinets.
Condo in Waltham
4.92 out of 5 average rating, 195 reviews

New Super Modern 2 bed in Waltham

A tastefully decorated unit on the 1st floor. Just across from the Waltham Watch Factory. 10-min walk to Moody St. and Charles River path. Built in 2014, open living, dining, and kitchen areas are ideal for working or entertaining. Stainless steel appliances and high class kitchenware. Spacious 2 bedrooms and 1 bathroom. Private deck. In unit washer/dryer. Baby friendly. Parking spot#1. Tax of 11.7% starts 7/1/19. Open and no-contact fire stairway is accessible from the parking lot.

Top Guest favourite
Home in Weston
4.97 out of 5 average rating, 108 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). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Top Guest favourite
A cozy sitting area is featured, highlighting a colorful area rug with abstract designs. Above the unit, art pieces in vibrant colors adorn the walls. A compact fridge and microwave are included, providing convenience for snacks and drinks.
Guest suite in West Newton
4.93 out of 5 average rating, 241 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
A spacious living area features soft furnishings with patterned upholstery and a light-colored coffee table. Natural light filters through the large windows draped with sheer curtains. The kitchenette is visible, along with a small dining table and chairs, creating a welcoming environment.
Apartment in West Newton
4.96 out of 5 average rating, 446 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!

Guest favourite
A well-lit bedroom features a spacious bed adorned with patterned bedding. Natural light filters through two large windows with wooden blinds, illuminating the soft carpeted floor. A bedside lamp provides additional warmth, and a door is partially visible on the right.
Guest suite in Wellesley
4.81 out of 5 average rating, 339 reviews

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

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
A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.
Guesthouse in Framingham
4.97 out of 5 average rating, 317 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.

Popular amenities for Weston holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Weston?

    Weston has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Weston have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Weston?

    Four-legged friends are welcome in Weston. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Where should I stay in Weston?

    Make yourself at home in Weston by choosing from our most frequently booked neighborhoods. We have over 340 vacation rentals in Newton Lower Falls, over 340 vacation rentals in Brandeis, and over 340 vacation rentals in Wellesley Farms.

  • How much does it cost to stay in apartment rentals in Weston?

    Experience the best of Weston with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Weston?

    Yes! Work meets play with ease at over 30 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Weston have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Weston?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Weston have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Weston have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Weston. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Weston

  • Total holiday rentals

    Explore 60 holiday rentals in Weston

  • Nightly prices starting at

    Weston holiday rentals start at $49 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Weston holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Weston rentals

  • 4.8 Average rating

    Weston stays are highly rated by guests—averaging 4.8 out of 5!

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