Weston holiday lettings

We found 1,452 holiday rentals — enter your dates for availability

Discover a selection of 14 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:6 Mar - 13 Mar

Image gallery for Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Fully stocked kitchen with plenty of room to prepare a family dinner
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

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

Chester, VT

7% off
Price is £3,096
for 7 nights, 1 chalet
£442 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Find spaces that suit your style

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:

  • Stratton Mountain Resort (14.4 mi / 23.2 km)
  • Viking Nordic Center (4.5 mi / 7.3 km)
  • Magic Mountain Ski Resort (6.7 mi / 10.8 km)
  • Stratton Mountain Golf Course (8.4 mi / 13.5 km)
  • Okemo Mountain Resort (8.5 mi / 13.7 km)
  • Bromley Mountain Ski Resort (8.8 mi / 14.1 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 the best area to stay. This charming locale is home to a delightful array of historic buildings and picturesque scenery, making it an ideal base for exploring the region. The Weston Playhouse Theatre Company is a top attraction here, providing a vibrant cultural experience with a variety of performances throughout the year. Additionally, the Weston Village Store offers a quaint shopping experience, where you can find local products and artisanal goods that capture the essence of Vermont.

Another lovely option is the surrounding countryside, where you can find numerous holiday rentals located amidst the rolling hills and beautiful landscapes. This area typically features a range of properties, from cosy cabins to elegant homes, providing ample choice for visitors seeking tranquillity and a connection to nature. Staying here allows easy access to outdoor activities such as hiking and skiing, particularly at nearby areas like Okemo Mountain Resort, ensuring a superb blend of relaxation and adventure.
How much does it cost to rent a holiday home in Weston?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Weston to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Weston holiday house rentals?
You can find great discounts on house rentals in Weston on Vrbo, 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.
Where are the best Weston ski resort rentals?
For the best ski resort rentals in Weston, Vermont, travellers should focus on the area surrounding the Okemo Mountain Resort, which is approximately a short drive away. In the village of Weston itself, visitors can find charming cottages and lodges that provide a quintessential New England experience. Many of these properties feature amenities such as fireplaces, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking to unwind after a day on the slopes.

Just a bit further afield, the nearby towns of Ludlow and Cavendish offer a wider selection of ski resort options, with lodgings ranging from modern condos to rustic chalets. These accommodations often come with additional perks like private balconies, outdoor grills, and access to hot tubs or swimming pools. The proximity to the ski areas allows guests to maximise their time on the mountain.
What is the most popular type of holiday rental accomodation in Weston?
In Weston, holiday houses are the most popular type of rental accommodation, with about 17 available throughout the area. These properties typically offer spacious living areas, fully equipped kitchens, and often come with outdoor decks or gardens, superb for enjoying the picturesque Vermont scenery. Additionally, there are several cabins, cottages, and chalets scattered around, providing a charming rustic feel that many travellers seek when visiting this quaint village. These alternatives often feature warm, cosy interiors and may include amenities like fireplaces and hot tubs, making them ideal for families or groups looking to relax after a day of exploring the surrounding countryside.
Are there any family house rentals in Weston?
In Weston, Vermont, there are numerous family-friendly house rentals available, with around 16 options scattered throughout the area. This picturesque town is known for its charming New England atmosphere and stunning natural surroundings, making it an ideal choice for families seeking a memorable getaway. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to enjoy.
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. This picturesque town, known for its charming New England architecture and scenic landscapes, offers a serene getaway. Many of these properties come equipped with amenities such as private pools, outdoor hot tubs, spacious decks for relaxing, and well-appointed kitchens, making them great for family gatherings or a peaceful retreat with friends.
Can I find long-stay holiday rentals in Weston?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Weston?
In Weston, there are several pet-friendly house rentals available, making it a delightful destination for travellers with furry companions. The area is known for its picturesque New England charm, with holiday homes often featuring amenities such as spacious living areas, well-equipped kitchens, and outdoor spaces great for enjoying the serene surroundings. Many properties offer cosy fireplaces, ideal for those chilly Vermont evenings, and some may even have private gardens where pets can roam freely.
Are there any remote work holiday rentals in Weston?
In Weston, Vermont, there are numerous remote work-friendly holiday rentals available, with around 22 options to choose from. This picturesque town, located in the Green Mountains, offers a serene environment that is ideal for productivity. Many of these properties come equipped with essential amenities for remote work, including dedicated office spaces, desks, ergonomic chairs, and reliable Wi-Fi, ensuring a comfortable work-from-home experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Weston holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in Weston?
In Weston, holiday rentals commonly feature essential amenities that cater to guests' needs. Most rooms include well-equipped kitchens, allowing for the preparation of meals during your stay. You'll typically find cookware, dishware, and utensils provided, along with microwaves and stovetops for convenient cooking. Refrigerators are also standard, ensuring that you can store food and beverages easily.
When is the best time to visit Weston for a holiday rental?
The best time to visit Weston for a holiday rental is in September, when the summer crowds begin to dwindle, and the breathtaking beauty of autumn starts to unfold. This month offers a superb blend of comfortable temperatures, usually around the mid-teens Celsius, and stunning fall foliage, making it ideal for outdoor activities and leisurely strolls through the charming town.

July through September marks the peak tourist season in Weston, with visitors flocking to enjoy the vibrant local events, farmer's markets, and picturesque landscapes. September, in particular, strikes a balance between lively tourist activity and a more relaxed atmosphere, allowing you to enjoy the scenic beauty without the hustle and bustle of the height of summer.

If you're considering a more budget-friendly option, February can be a great time to visit, as it falls within the low season. While temperatures may dip to around freezing, this serene period offers a unique opportunity to experience Weston's winter charm, including snow-covered landscapes and quieter hiking trails.
How early should I book a Weston holiday rental?
Book your Weston holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Weston home rental booking on Vrbo?
To find Weston holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Weston holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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