
Holiday houses in Weston
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Top-rated holiday rentals in Weston
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Little Cabin on the Ridge
Classic Vermont cabin.This cozy home is perfect for singles, couples and families.The well-designed space offers sleeping for 4 in two bedrooms and an open loft space. Wrap around porch has 4 rockers for taking in the mountain air, coffee or tea, or reading in a cozy quilt. Fiber optic wifi 1000 mbps.Very efficient forced hot air heating and Central Air cooling.Peaceful, quiet,relaxing, great place to unwind with all kinds of activities nearby. due to health and safety concerns no animals please

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. Xfinity high speed Internet and streaming TV. Private entrance from deck or shared entrance via front door.

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

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!

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

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 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.

The Owl’s Nest in Landgrove
Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

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. I am as close or as far away as you would like me to be with my house right next door.

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!

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.
Popular amenities for Weston holiday rentals
Other great holiday rentals in Weston

Charming Vermont Schoolhouse

Old School Ski Haus

10 Min to Stratton Resort | Private Hot Tub

Just an Incredible Vermont Mountain Retreat

Peaceful Chalet In Londonderry

Ground Floor, Okemo True Ski-in/Ski-Out

Cozy Family/Pet Friendly Cabin w/ Modern Upgrades

VT Cabin sitting above the West River and Village
When is the best time to visit Weston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $500 NZD | $605 NZD | $480 NZD | $419 NZD | $387 NZD | $365 NZD | $505 NZD | $380 NZD | $482 NZD | $494 NZD | $559 NZD | $614 NZD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Frequently Asked Questions
Are there house rentals with a dedicated workspace in Weston?
Yes! Work meets play with ease at over 20 house rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Weston?
Weston has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Weston have a kitchen?
Absolutely! We offer over 40 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 40 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 40 house rentals with free parking in Weston. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Weston?
Experience the best of Weston with our house rentals, starting at about $150 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 house rentals in Weston?
Four-legged friends are welcome in Weston. Choose from more than 20 house rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Weston?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 40 homes with free parking, over 40 homes with a kitchen, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Weston

Total holiday rentals
Explore 60 holiday rentals in Weston

Nightly prices starting at
Weston holiday rentals start at $167 NZD per night before taxes and fees

Verified guest reviews
Over 3,020 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Weston holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Weston rentals

4.9 Average rating
Weston stays are highly rated by guests—averaging 4.9 out of 5!
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Mount Sunapee Resort
- Dartmouth College
- Mount Monadnock
- Trout Lake
- Massachusetts Museum of Contemporary Art




