Holiday rentals in Weston

4.94 out of 5 average rating, 348 reviews

Cabin in Londonderry

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. 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!

4.96 out of 5 average rating, 265 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!

4.98 out of 5 average rating, 130 reviews

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

4.97 out of 5 average rating, 100 reviews

Cottage in Weston

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

4.97 out of 5 average rating, 165 reviews

Apartment in Stratton

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

4.94 out of 5 average rating, 1,270 reviews

Tiny home in Jamaica

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. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Guest house in Wallingford

4.98 out of 5 average rating, 699 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!

4.99 out of 5 average rating, 646 reviews

Barn in Chester

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.

Superhost

Guest suite in Weston

4.97 out of 5 average rating, 220 reviews

Spacious King Spa Suite Weston Hills

Spacious 750 sqft guest suite king bed, table & chairs, kitchenette & sitting area & large, private spa bathroom featuring walk through mosaic shower area 4 shower heads, jets, wands & two person roman jacuzzi tub featuring aroma & chroma therapy & heated back rests. Ensuite bidet, elongated toilet & urinal. Pull-out sofa & comfy king bed with views from 5 glass doors to private deck. Internet and streaming TV with Peacock Premium. Private entrance from deck.

4.9 out of 5 average rating, 120 reviews

Tiny home in Athens

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

4.99 out of 5 average rating, 135 reviews

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

4.98 out of 5 average rating, 429 reviews

Flat in Andover

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!

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Other great holiday rentals in Weston

5 out of 5 average rating, 8 reviews

Home in Tinmouth

Charming Vermont Schoolhouse

RobinRating, 5 stars4 days ago

My husband and I absolutely loved staying at Scott’s beautifully remodeled Schoolhouse. Scott was super responsive and very flexible for our arrival. Upon arrival the we were pleasantly surprised and greeted by a very friendly Rooster! We also loved how spotless and immaculate the entire house was. We loved the spaciousness and we felt right at home. Bed was super comfortable and Scott and his wife had thought of every possible little thing that you might need in the bathroom. We also had a welcome basket of goodies that we really enjoyed. I highly recommend that you book this place! You will not be disappointed. In fact we have already booked it for a return trip in August. We loved the large windows and decor of the home. You can tell that they put a lot of thought into making this a comfortable and relaxing space. Kitchen was also well appointed. Location was very quiet and peaceful. This place is top notch!

4.64 out of 5 average rating, 33 reviews

1BR mountain view retreat with kitchenette

GenRating, 5 stars2 weeks ago

Super beautiful spot, has certified my dream of moving to VT down the line. Beautiful neighborhood, friendly people all around town, cows right up the street, and the yard felt like a mini paradise! Perfect for morning yoga, coffee, reading a good book, or any of your tiny hobbies you’d like to enjoy outside :) The bathroom was clean and adorable, the kitchen was the perfect size! The stove can be a little tricky if you aren’t used to the model but nothing a quick youtube video on how it works didn’t fix! I cant recommend this place enough, just don’t book it solid I’d like to stay here again soon on my next visit

Flat in Londonderry

4.92 out of 5 average rating, 368 reviews

Cozy Suite in a Historic Building Near Ski Resorts

DylanRating, 5 stars2 weeks ago

Staying at Jason’s cozy suite in Londonderry was an absolute treat. The space was warm, clean, and thoughtfully arranged, perfect for unwinding after a day of exploring the Green Mountains. Everything from the comfortable bed to the charming rustic touches made it feel like a true Vermont escape. Jason was a great host! Very responsive, welcoming, and respectful of privacy. The location was ideal: close to local trails, ski spots, and great small-town food, but still tucked away enough to enjoy some real quiet. Highly recommend for anyone looking to slow down and soak in the calm beauty of Vermont. I’d definitely stay again.

4.85 out of 5 average rating, 33 reviews

Historic Rideout 16m to Okemo Walk to Town

WarrenRating, 5 stars8 months ago

The place was great for our friend-reunion. We have a bunch of little kids and he space worked well for 5 families. Lots of bedrooms and far enough from common spaces that they were very quiet. The open kitchen/living room was our hub. The fireplace provided a great ambiance. The house is older, charming, and well taken care of. Weston is a classic southern VT town. Fun to walk into town for VT country store, ice cream, etc. There is also a playground that is open to the public at The Little School in town. Town Green is also a good place to hang out. It worked well for our little ones.

4.95 out of 5 average rating, 84 reviews

Cabin in Andover

Little Cabin on the Ridge

JoshRating, 5 stars2 months ago

Beautiful home and area, very quiet and comfortable. Kelly is communicative and helpful. Thanks for having us and we'd definitely enjoy coming again!

5 out of 5 average rating, 11 reviews

Home in Peru

Highland Haus: stunning ski getaway with hot tub

AbigailRating, 5 stars3 weeks ago

The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

4.98 out of 5 average rating, 61 reviews

Home in Mount Holly

Breathtaking VT Getaway

KerryRating, 5 stars4 months ago

House and location - the house is beautiful and the view from the backyard is amazing. The location was as described. It was also great that the host shared that the cell service around the house is poor. Amenities - the amenities were great. We cooked while we stayed and the kitchen was fully stocked with anything we could possibly need. Including things like serving platters and bowls. It was also great that the fireplace was useable and stocked with wood. Extra - it snowed like crazy when we stayed. Having the plow service helped us in the driveway greatly! One edit to the listing - Belmont General Store was closed when we stayed.