Vacation rentals in Weston

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Top-rated vacation rentals in Weston

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Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov. 5 – 12

$164 CAD per night

Guest favourite

Home in Weston

4.95 out of 5 average rating, 227 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Aug. 23 – 30

$404 CAD per night

Guest favourite

Home in Weston

4.86 out of 5 average rating, 106 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Oct. 12 – 19

$250 CAD per night

Guest favourite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

May 1 – 8

$162 CAD per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Aug. 25 – Sep. 1

$161 CAD per night

Guest favourite

Guesthouse in Wallingford

4.98 out of 5 average rating, 589 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Dec. 19 – 26

$218 CAD per night

Guest favourite

Condo in Ludlow

4.92 out of 5 average rating, 123 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

May 12 – 19

$168 CAD per night

Guest favourite

Guest suite in Mt Holly

4.98 out of 5 average rating, 117 reviews

Exquisite Green Mountain Loft Haven

Lovely apartment in country home affords privacy plus all the necessities of home. Beautiful grounds and views afford relaxation and invigoration. Ski at local ski resorts or snowshoe or sled right outside your door. Comfortable beds, peace and quiet, and dark skies means great sleeping. Fully stocked kitchen, and nearby summer activities makes staying here fun and enjoyable. Come find out what others already know!!

Nov. 12 – 19

$215 CAD per night

Guest favourite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep. 23 – 30

$175 CAD per night

Guest favourite

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

May 25 – Jun. 1

$178 CAD per night

Guest favourite

Tiny homes in Jamaica

4.94 out of 5 average rating, 1143 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate.

Nov. 7 – 14

$151 CAD per night

Superhost

Apartment in Weston

4.86 out of 5 average rating, 129 reviews

Cozy Guesthouse in Heart of VT

Welcome The cozy charm of Simple Living Guesthouse will make you feel right at home from the moment you step inside. Fully furnished, clean inviting Sleeps 3 Newly remodeled bath We are located on VT scenic rt 100, a popular rte Vermont Meals and Rooms Tax ID number is MRT-10126712

Aug. 6 – 13

$168 CAD per night