
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.

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
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
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
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
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
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
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
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
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
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
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
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 reviewsPopular amenities for Weston holiday rentals
Stay near Weston's top sights
Other great holiday rentals in Weston

Bright, sunny 1 bedroom condo
4.89 out of 5 average rating, 61 reviews
Bright Private Quiet Apartment – 30 min to Boston
4.93 out of 5 average rating, 15 reviews
Cozy & convenient place with sunset & garden view
4.95 out of 5 average rating, 37 reviews
Escape the city and enjoy the serenity of Weston
5.0 out of 5 average rating, 19 reviews
New! 2BR Home Metro West
5.0 out of 5 average rating, 10 reviews
Family-Friendly 4BR Near Boston, Walk to Moody St
4.94 out of 5 average rating, 17 reviews
Private suite 1 BR, 1 BA, 1 LR, 1 FLR
4.8 out of 5 average rating, 371 reviews
18 Mi to Boston - Stylish Unit in Upscale Enclave!
4.83 out of 5 average rating, 6 reviewsFrequently 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.
Destinations to explore
- Fenway Park
- Hampton Beach
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- Duxbury Beach
- North Hampton Beach
- MIT Museum
- Harvard Square
- Tufts University
- Crane Beach
- Quincy Market
- Snhu Arena
- Massachusetts Institute of Technology





