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Holiday rentals in Weston

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Weston

  • Total holiday rentals

    Explore 70 holiday rentals in Weston

  • Nightly prices starting at

    Weston holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    70 of Weston holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Weston rentals

  • 4.8 Average rating

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

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 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
4.98 out of 5 average rating, 135 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. 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. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood

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
5 out of 5 average rating, 207 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
A living area features a comfortable sofa with cushions, a glass coffee table, and a flat-screen TV on a stand. A round dining table with wooden stools is visible, along with a large mirror reflecting the space. Sunlight enters through sheer curtains.
Flat in Waltham
4.98 out of 5 average rating, 120 reviews

Just Renovated, Private & Quiet 2 Bedroom Condo

Keep it simple and comfortable at this peaceful, centrally located getaway. Set at the very end of a private, ultra-quiet dead-end road, the home feels tucked away This newly renovated 2-bedroom unit is an ideal home base for your Boston-area stay You’ll have easy access to public transportation, parks, dining, shopping, and major highways including I-95, I-90, and Route 2. Enjoy your own private outdoor deck, a spacious yard, in-unit laundry, central AC, and off-street parking for two cars

Guest favourite
Flat in Woburn
4.94 out of 5 average rating, 249 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

Top guest favourite
Home in Wayland
5 out of 5 average rating, 7 reviews

New! 2BR Home Metro West

Brand-new, sleek and contemporary 2-BR home near Boston — private, peaceful, and perfect for couples, professionals, or students. 17 MILES TO GILLETTE STADIUM!! This brand-new, stand-alone tiny home in Wayland is contemporary, bright, and clean. Flexible layout: two bedrooms or one plus an office, perfect for couples, visiting family, professors, or students. Full kitchen and bath, located in a peaceful, wooded neighborhood, just 15 miles from downtown Boston with easy access to Route 90.

Top guest favourite
A living area features a large wall adorned with natural-themed artwork, complemented by two windows allowing ample light. A flat-screen TV is mounted on the wall opposite a small table with a woven texture. A plush gray sofa enhances the inviting space.
Serviced apartment in Newton
5 out of 5 average rating, 117 reviews

Inn at Newton Highlands, Suite 2, Apartment-Hotel

This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

Top guest favourite
The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.
Home in Weston
4.97 out of 5 average rating, 118 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...

Guest favourite
Home in Framingham
4.97 out of 5 average rating, 156 reviews

1BR Loft | 25 Mins to Boston | Quiet Neighborhood

Welcome to The Loft! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Mattress Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Essentials Dining Area — Table & Chairs Living Room — Leather Sofa 49" SmartTV — Netflix + Sling Live TV Bathroom — Shower, Plush Towels & Natural Bath Products Private 2nd Floor Entrance Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized 2 Min Walk to Park 25 Mins to Boston Easy Access —Route 9 & 90-Mass Pike

Guest favourite
Home in Wayland
4.9 out of 5 average rating, 132 reviews

Spacious 4 bedroom home with large yard

Private and clean renovated 4 bedroom house in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 8 comfortably in 4 bedrooms. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Kids will enjoy the swingset. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27, and many colleges and MetroWest office parks.

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, 358 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. NEW in 2022: Mini-split AC!

Top guest favourite
A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.
Guest suite in Lexington
4.97 out of 5 average rating, 182 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

Guest favourite
The living area is furnished with a soft sofa and decorative throw pillows, complemented by a patterned area rug. Natural light enters through sheer curtains, creating a bright and welcoming ambiance. A dining table with wooden chairs is visible in the adjoining space.
Home in Waltham
4.78 out of 5 average rating, 493 reviews

Beautiful, Clean & Quiet 2 BR- 15 min to BOSTON

SUNNY, CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College. FREE PARKING, WiFi and WASHER & DRYER.

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.

  • 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 pet-friendly vacation rentals in Weston?

    Four-legged friends are welcome in Weston. Choose from more than 30 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 50 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Weston hotel rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!

  • 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.

  • Do house rentals in Weston have a kitchen?

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

  • Do house rentals in Weston have wifi?

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

  • Do house rentals in Weston have free parking?

    Absolutely! We offer over 20 house rentals with free parking 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 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.