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Holiday houses 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 $87 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    70 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!

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

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

4.98 out of 5 average rating, 141 reviews
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

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.

5.0 out of 5 average rating, 211 reviews
Guest favourite
A cozy living area features a dark sectional sofa and a light wood coffee table positioned on a textured area rug. A television is mounted on the wall across from the seating, complemented by a small lamp on a side table. Natural light filters through multiple small windows.
Apartment in Wayland

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

4.89 out of 5 average rating, 56 reviews
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.
Apartment in Waltham

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

4.98 out of 5 average rating, 122 reviews
Superhost
A spacious living area features two gray sofas with yellow accent pillows, arranged around a circular wooden coffee table. A gas fireplace is centered against a white mantel, complemented by large windows allowing natural light and views of greenery.
Townhouse in Waltham

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. Just 1 min walk to Waltham Rail Station (some ambient rail sounds possible), buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

4.93 out of 5 average rating, 162 reviews
Superhost
A spacious bedroom features two neatly made beds, one larger and one smaller, adorned with white bedding. A bedside table holds a lamp, and a window with light curtains allows natural light to enter, complemented by warm LED ceiling lights.
Condo in Waltham

Lovely one bedroom apartment condo, with parking

The whole group will enjoy easy access to everything from this centrally located place. Entire unit. In the heart of Waltham Large and comfortable one bedroom apartment in quite condominium style place. Great location 5 minutes walk to train or bus to Boston, 6 minutes walk to Moody street where all the restaurants and attractions are currently open. Also 7 minutes drive from Brandeis university or Bentley College . We are located near everything you would need to do in Waltham. The

4.84 out of 5 average rating, 152 reviews
Top Guest favourite
The living room features two dark leather sofas arranged around a circular glass coffee table. Natural light enters through large windows adorned with light-colored drapes. A mirror on the wall complements the warm beige walls, enhancing the space's cozy atmosphere.
Home in Wayland

Quiet & Cozy 4 BR in Metrowest- 25 mins to Boston

Keep it simple at this peaceful and centrally-located home. Cozy, quiet & clean 4 bedroom and 2 bathroom home conveniently located in the Metrowest area- 25 minutes to Boston. Situated in a very quiet neighborhood, close to grocery stores, restaurants and shopping. Guests will have access to the entire home excluding the garage. * Free parking * Free high speed internet/WiFi * Premium Cable channels * Basic cookware & dinnerware * Access to free Washer & Dryer * Keypad Entry System

4.94 out of 5 average rating, 186 reviews
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.
Apartment in Newton

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.

5.0 out of 5 average rating, 120 reviews
Top Guest favourite
A spacious living area features hardwood flooring and large glass doors that provide natural light and views of the outdoors. Two comfortable sofas are positioned around a coffee table, with a dining area visible in the background. Wall sconces add soft illumination.
Home in Weston

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...

4.97 out of 5 average rating, 120 reviews
Guest favourite
Home in Wayland

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.

4.89 out of 5 average rating, 133 reviews
Guest favourite
The exterior of a Victorian-era home is surrounded by lush greenery, with vibrant flowers lining the pathway. A spacious porch is visible, framed by tall trees, inviting guests to enjoy the natural setting. A gravel driveway leads to the welcoming entrance.
Home in Waltham

Harvard House-The Gathering Place.

HARVARD HOUSE - The Gathering Place--- Winter Specials for single rooms Jan-March-20% off A magical atmosphere ideal for small weddings, birthdays, graduations, celebrations of life. team building "Harvard House is an amazing place, it helped our family renew the ties that bind." "The team created a shared vision, conflicts got ironed out, we built a rallying momentum." "Our wedding at Harvard House was amazing." "Our group split the costs which made it affordable."

4.94 out of 5 average rating, 111 reviews
Guest favourite
Home in Framingham

Retreat Near Boston | AC, BBQ, Deck, Pets OK

Welcome to your perfect home base just outside Boston—ideal for families, groups, and business travelers alike. This bright and spacious 4-bedroom home comfortably accommodates your group with 7 beds and plenty of room to relax. Enjoy a large, sun-filled living area, a bonus dining space with beautiful vaulted ceilings, and a fully equipped kitchen with modern stainless steel appliances—perfect for gathering and entertaining.

4.92 out of 5 average rating, 12 reviews

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.