Weston holiday rentals

We found 1,465 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Weston that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Weston

Showing deals for:18 Dec - 25 Dec

Living area
Property grounds
Exterior
Interior
Exceptional
(48 reviews)

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Ludlow

8% off
AU$8,594
for 7 nights, 1 chalet
AU$1,228 per night
includes taxes & fees
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Welcome to the Blue Moon Bungalow!
Fully stocked kitchen with plenty of room to prepare a family dinner
Bear Room - 2nd Floor bedroom with a king bed, tv with roku and sitting area.
Deer Room - 1st floor bedroom with a queen bed.
Exceptional
(11 reviews)

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester

8% off
AU$4,933
for 7 nights, 1 chalet
AU$705 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Pool
Living area
Property grounds
Private kitchen
Exceptional
(16 reviews)

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish

8% off
AU$16,374
for 7 nights, 1 cabin
AU$2,339 per night
includes taxes & fees
Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
Exterior
Exterior
Interior
Private kitchen
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
AU$35,082
for 7 nights, 1 home
AU$5,012 per night
includes taxes & fees
Beautiful Lakeview Log Cabin on 60-Acre Property
Dining room
Living area
Front door
Back porch
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
AU$3,747
for 7 nights, 1 cabin
AU$535 per night
includes taxes & fees
Wishing Well Cabin
Sitting room looking into the kitchen.
Interior
Private kitchen
View from upstairs guest room
Exceptional
(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off
AU$15,575
for 7 nights, 1 home
AU$2,225 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
A look at the main floor family room from above.
Welcome to our 9 bedroom luxury home in the heart of Southern Vermont!
Complete privacy on our property!
Hot tub and firepit are great after a day of fun.
Exceptional
(22 reviews)

Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!

Bondville

8% off
AU$38,556
for 7 nights, 1 home
AU$5,508 per night
includes taxes & fees
Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!
Den area main level (baby not included!)
Master bedroom looking Southwest (upper level
Kitchen (main level)
Winter looking Southeast
Exceptional
(25 reviews)

All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!

Mount Holly

8% off
AU$5,772
for 7 nights, 1 cabin
AU$825 per night
includes taxes & fees
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!
Exterior
Living area
Interior
Private kitchen
Exceptional
(16 reviews)

Okemo Mountain View Retreat

Cavendish

8% off
AU$10,105
for 7 nights, 1 home
AU$1,444 per night
includes taxes & fees
Okemo Mountain View Retreat
Exterior
Porch -Summer
Antique Cabin
Antique Cabin
Exceptional
(89 reviews)

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Jamaica

8% off
AU$5,953
for 7 nights, 1 home
AU$850 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Dining area
Large open-concept living and kitchen area
Terrace/patio
Bedroom 1: Queen Bed
Exceptional
(18 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

8% off
AU$8,548
for 7 nights, 1 cabin
AU$1,221 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Interior
Exterior
Living area
Private kitchen
Wonderful
(5 reviews)

Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit

Ludlow

6% off
AU$12,714
for 7 nights, 1 home
AU$1,816 per night
includes taxes & fees
Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit
Dining
Interior
Bar (on property)
Private kitchen
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
AU$24,265
for 7 nights, 1 home
AU$3,466 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Covered outdoor patio with views of the lake, connecting to king bedroom
Front of home (late fall sunset)
The Great Room and dining table - seats 10
View (summer) from the covered / screened-in outdoor patio
Exceptional
(20 reviews)

5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C

Ludlow

8% off
AU$15,358
for 7 nights, 1 home
AU$2,194 per night
includes taxes & fees
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
2nd - 3rd floor main house stairs
Main house top floor river room with sounds of the river out the windows.
Main house top floor river room with deck overlooking the pool and backyard.
View of the Main house living room from the kitchen bar
Exceptional
(38 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

8% off
AU$21,991
for 7 nights, 1 home
AU$3,142 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Main dining space with seating for 12
IMG 1540
Fully stocked kitchen with breakfast nook and island
Outdoor dining
Exceptional
(7 reviews)

Stylish new A Frame with Lake Rescue dock access

Ludlow

8% off
AU$7,787
for 7 nights, 1 home
AU$1,112 per night
includes taxes & fees
Stylish new A Frame with Lake Rescue dock access
Private kitchen
Exterior
Dining
Plenty of room for relaxing.
Exceptional
(33 reviews)

Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.

Bondville

8% off
AU$9,178
for 7 nights, 1 chalet
AU$1,311 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
Exterior
Interior
Dining
Private kitchen
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
AU$17,704
for 7 nights, 1 home
AU$2,529 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Open living room with french doors, huge windows & vaulted ceiling
Front of house, early spring
Light filled kitchen
Bedroom #2 Queen bed with large windows & french doors
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
AU$5,835
for 7 nights, 1 home
AU$834 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Yoga Studio
Chef's Kitchen
Dining area
Front of House - Summer
Exceptional
(60 reviews)

Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!

Plymouth

14% off
AU$14,991
for 7 nights, 1 home
AU$2,142 per night
includes taxes & fees
Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!
front porch with Adirondack chairs and a snowboard bench and icicle lights
Interior
Living room w/TV Cable, game table, games, local magazines, & electric fireplace
Enter through mud room door from the driveway
Exceptional
(60 reviews)

Victorian Village Home in Town! with access to shuttle service to Okemo.

Ludlow

12% off
AU$9,913
for 7 nights, 1 home
AU$1,416 per night
includes taxes & fees
Victorian Village Home in Town! with access to shuttle service to Okemo.
let it snow!
Outdoor dining
Stratton mtn fire tower view
living room
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

8% off
AU$5,493
for 7 nights, 1 home
AU$785 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
Living area
Pool in the nearby recreational building
Living area
Dining
Exceptional
(140 reviews)

Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace

Ludlow

8% off
AU$18,447
for 7 nights, 1 apartment
AU$2,635 per night
includes taxes & fees
Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace
Exterior
Terrace/patio
Interior
Interior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off
AU$10,107
for 7 nights, 1 home
AU$1,444 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Head to the relaxing city of Weston

Enjoy the area's entertainment, theatre scene and museums with a rental holiday home in Weston. This relaxing and scenic city is well known for its skiing, hiking and shopping. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Weston

Are you hoping to discover top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that makes Weston a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Viking Nordic Center (4.5 mi / 7.3 km)
  • Magic Mountain Ski Resort (6.7 mi / 10.8 km)
  • Okemo Mountain Resort (8.5 mi / 13.7 km)
  • Bromley Mountain Ski Resort (8.8 mi / 14.1 km)
  • Fox Run Golf Course (9.8 mi / 15.7 km)
  • Jamaica State Park (10 mi / 16.1 km)

Exploring the natural landscape of Weston

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Weston. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Lowell Lake State Park (4.9 mi / 7.9 km)
  • Buttermilk Falls (10.5 mi / 16.9 km)
  • Emerald Lake State Park (10.7 mi / 17.2 km)
  • Green Mountain National Forest (10.8 mi / 17.4 km)
  • Lake Rescue (12 mi / 19.3 km)
  • Echo Lake (13.4 mi / 21.6 km)

Transport to and around Weston

The nearest airport is in Springfield, VT (VSF-Hartness State), located 14 mi (22.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 18 mi (29 km) away.

Frequently asked questions

What is the best area to stay in Weston when booking a holiday rental?
When considering a holiday rental in Weston, Vermont, the village centre is a popular area to stay. This charming hamlet exudes a quintessential New England vibe, complete with picturesque landscapes and a rich sense of history. The village is home to around 100 properties available for holiday rentals, suiting a variety of preferences and budgets.Staying in the village centre means you'll be just a stone's throw away from the renowned Weston Playhouse Theatre Company, which offers an array of performances that highlight local talent and creativity. Additionally, the Weston Village Store is a delightful spot to explore, providing an assortment of local goods, artisanal products, and delicious treats.For those who appreciate the beauty of nature, the nearby Green Mountain National Forest offers stunning hiking trails and scenic vistas, superb for outdoor enthusiasts.
Where are the best Weston ski resort rentals?
For ski resort rentals in Weston, Vermont, the area around the Okemo Mountain Resort is a prime choice, as it is relatively close and offers exceptional skiing opportunities. In Weston itself, visitors can find a range of charming cabins and lodges that exude New England character. Many of these properties come equipped with amenities such as wood-burning fireplaces, spacious living areas, and well-appointed kitchens, superb for unwinding after a day on the slopes.The nearby village of Ludlow offers additional options, where you can discover more contemporary condos and ski-in/ski-out accommodations that provide convenient access to the slopes. These rentals often include features like hot tubs and access to shared amenities such as pools and fitness centres, enhancing the overall experience for travellers.Additionally, the picturesque town of Weston is known for its quaint atmosphere and artistic community, making it a great base for those looking to explore local shops and eateries. The charming Weston Playhouse Theatre Company, which hosts a variety of performances, adds to the cultural appeal of the area. Rentals in this region may also have outdoor spaces, allowing guests to enjoy the serene natural surroundings.
What is the most popular type of holiday rental accomodation in Weston?
In Weston, holiday houses are the most prevalent type of holiday rental, with around 48 available throughout the charming town. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often include outdoor areas for relaxing after a day of exploring the scenic countryside. Cottages also have a great presence, with about 16 options that provide a quaint, rustic feel superb for couples or small families seeking a cosy retreat. Additionally, there are around 12 cabins and several chalets, which offer a great experience amidst nature, often including amenities such as fireplaces and access to hiking trails.
Are there any family house rentals in Weston?
In Weston, Vermont, there are some family-friendly house rentals available, with approximately 15 options to choose from. This charming area is known for its picturesque landscapes and close proximity to various outdoor activities. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for children to play. Visitors can expect amenities such as Wi-Fi, laundry facilities, and some homes even have fireplaces, adding a cosy touch for chilly evenings.Weston is ideally situated near attractions like the Weston Playhouse Theatre Company, where families can enjoy live performances, as well as the scenic trails of the Green Mountains for hiking and skiing adventures. The village itself offers a quaint atmosphere, with local shops and eateries providing an authentic Vermont experience.
Can I rent a holiday home with a pool or hot tub in Weston?
In Weston, Vermont, there are several holiday homes available for rent that feature pools or hot tubs, providing an excellent option for those looking to unwind in a serene environment. This charming village is set against the backdrop of the Green Mountains, offering a picturesque setting for your getaway.Travellers can expect amenities such as private pools, hot tubs, and spacious outdoor areas, great for enjoying the fresh mountain air. Many properties also come equipped with fully stocked kitchens, comfortable living spaces, and sometimes even fireplaces, adding to the cosy atmosphere.The area is ideal for both relaxation and exploration, with nearby hiking trails and the beautiful countryside inviting outdoor activities throughout the year.
Are there pet-friendly house rentals in Weston?
In Weston, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties come with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can play and explore.The charming village of Weston is surrounded by beautiful landscapes, offering a serene atmosphere great for relaxation. Additionally, the nearby Green Mountain National Forest presents plenty of opportunities for outdoor activities, including hiking trails that are suitable for walking with pets. The area is known for its picturesque scenery, making it an ideal destination for those looking to enjoy nature alongside their pets.
Are there any remote work holiday rentals in Weston?
In Weston, Vermont, there are numerous remote work holiday rentals available, with around 80 options to choose from. This picturesque town, known for its charming rural atmosphere and proximity to stunning landscapes, offers a variety of properties that cater to remote workers. Many rentals come equipped with essential amenities such as high-speed internet, dedicated workspaces with desks and chairs, and even printers for added convenience.Travellers can expect a mix of cosy cottages and spacious homes, often featuring fully equipped kitchens and comfortable living areas, allowing for a pleasant work-life balance. Additionally, the serene environment of Weston encourages relaxation after a day of work, with opportunities for outdoor activities like hiking and exploring the local scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Weston?
In Weston, popular holiday rentals typically feature a range of desirable amenities that enhance the comfort of guests. Most properties come equipped with kitchens, allowing travellers to prepare their own meals, which is particularly convenient for families or groups. Many rentals also include cosy fireplaces, superb for warming up after a day spent exploring the area's picturesque surroundings. Most properties offer outdoor spaces like decks or patios, providing a lovely spot to unwind while enjoying the fresh air. Onsite parking is another common amenity, making it easy for visitors to access their accommodations without hassle. Additionally, many rentals feature coffee and tea makers, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Weston for a holiday rental?
September is the most popular time to visit Weston, Vermont, as the autumn foliage begins to paint the landscape in vibrant hues. This month falls within the peak season, which spans from July to September, attracting visitors who seek both outdoor adventures and charming small-town experiences.During this period, temperatures are generally pleasant, ranging from the low teens to mid-20s Celsius, making it ideal for hiking and exploring local attractions. The picturesque trails and scenic byways offer an abundance of opportunities for sightseeing, allowing you to immerse yourself in the beauty of the Green Mountains.For those looking for a more budget-friendly option, February presents a fantastic opportunity to enjoy a quieter side of Weston. While this is considered the low season, visitors can still appreciate the serene winter landscape, superb for cosy getaways or cross-country skiing. The charming atmosphere of a winter retreat can be quite enchanting, with fewer crowds and the chance to truly relax.Ultimately, your choice of when to visit Weston will depend on whether you're drawn to the lively energy of the autumn season or the tranquil charm of winter.
What are the top attractions in Weston?
In Weston, Vermont, visitors can enjoy the charm of this picturesque village, particularly known for its historic buildings and quaint atmosphere. The Weston Playhouse Theatre Company offers a variety of performances throughout the year, making it a cultural hub for locals and tourists alike. The nearby Weston Village Store is a must-visit for its selection of local products and delightful cafés, superb for a leisurely afternoon.For those interested in outdoor activities, the surrounding Green Mountains provide ample opportunities for hiking and enjoying the stunning natural scenery. During the winter months, nearby ski resorts in the area cater to snow sports enthusiasts. Additionally, the annual Weston Craft Show showcases the work of local artisans, adding to the region's appeal for those interested in Vermont's crafts and culture.
Are all fees included in the Weston holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Weston holiday homes with parking?
Stayz offers a wide selection of holiday homes in Weston with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Weston holiday homes?
You can find great discounts on holiday homes in Weston on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Weston holiday home booking on Stayz?
To find Weston holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Weston?
A long-stay holiday home in Weston is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Weston holiday home?
Book your Weston holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Weston?
Prices for holiday homes in Weston vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Weston to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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