
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.

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

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.

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

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.

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!

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

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.

Conveniently Located Private Garden Apartment
Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

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...

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.

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."

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
Other great holiday rentals in Weston

Bright Private Quiet Apartment – 30 min to Boston

Bright and open modern farmhouse

The Clark : Aesthetic • Clean • Amenities!

2bed/2bath Apt at Waltham Landing. Corner Unit

Ipswich Waterfront Getaway

Quiet/Private Neighborhood

2BR Colburn Apartment | Near Market Basket & Plaza

Westwood Airbnb
Frequently Asked Questions
Are there family-friendly vacation rentals in Weston?
Weston has more than 20 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 vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Weston?
Make yourself at home in Weston by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Newton Lower Falls, over 310 vacation rentals in Brandeis, and over 310 vacation rentals in Wellesley Farms.
Do hotel rentals in Weston have air conditioning?
Absolutely! We offer over 10 hotel rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Weston have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.
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 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.
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 $68 NZD per night before taxes and fees

Verified guest reviews
Over 1,080 verified reviews to help you choose

Family-friendly holiday rentals
20 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, Wifi 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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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- New England Aquarium
- Brown University
- Revere Beach
- Boston Seaport
- Northeastern University
- Boston University
- Gillette Stadium
- Freedom Trail
- Boston Convention and Exhibition Center
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Quincy Market
- Roxbury Crossing Station
- Museum of Fine Arts
- North Hampton Beach
- Good Harbor Beach
- Boston College





