Wallingford holiday rentals

We found 737 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Wallingford that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Wallingford

Showing deals for:20 Nov - 27 Nov

Winter looking Southeast
Master bedroom looking Southwest (upper level
Kitchen (main level)
Den area main level (baby not included!)
Exceptional
(25 reviews)

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

Mount Holly

8% off
AU$5,508
for 7 nights, 1 cabin
AU$787 per night
includes taxes & fees
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!
Bedroom 1- King bed with private large bathroom attached
New living room furniture January of 2026. Sectional sofa. Smart TV.
We are and unit with the entrance on the ground floor
Living room. New smart TV. Dining area
Exceptional
(27 reviews)

A1 Solitude.4 BDRM, ski in/out to main Solitude lift, pool/gym access. Parking!

Ludlow

8% off
AU$11,681
for 7 nights, 1 home
AU$1,669 per night
includes taxes & fees
A1 Solitude.4 BDRM, ski in/out to main Solitude lift, pool/gym access. Parking!
Living area
Exterior
Interior
Terrace/patio
Wonderful
(5 reviews)

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

Ludlow

6% off
AU$12,813
for 7 nights, 1 home
AU$1,830 per night
includes taxes & fees
Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit
Outdoor dining
IMG 1540
Fully stocked kitchen with breakfast nook and island
Coffee options galore!
Exceptional
(7 reviews)

Stylish new A Frame with Lake Rescue dock access

Ludlow

8% off
AU$6,899
for 7 nights, 1 home
AU$986 per night
includes taxes & fees
Stylish new A Frame with Lake Rescue dock access
Front of House - Summer
Chef's Kitchen
Front of house in winter
Yoga Studio
Exceptional
(60 reviews)

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

Plymouth

14% off
AU$10,946
for 7 nights, 1 home
AU$1,564 per night
includes taxes & fees
Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!
Bedroom #2
Main deck
Entrance
Exterior
Exceptional
(29 reviews)

Lake Front home on Lake Rescue. Sunset views, peaceful home with a private dock.

Ludlow

8% off
AU$6,945
for 7 nights, 1 home
AU$992 per night
includes taxes & fees
Lake Front home on Lake Rescue. Sunset views, peaceful home with a private dock.
Main entryway. Bright and welcoming!
Welcome Bear ..... We'll Leave the Light on For You!
Beautiful Fall Foliage - See Video!
Large Bear Creek room, main level. New hi end queen, ceiling fan, picture window
Exceptional
(68 reviews)

OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14

Ludlow

8% off
AU$10,376
for 7 nights, 1 home
AU$1,482 per night
includes taxes & fees
OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14
2nd floor bathroom w/washer drier, 2 showers, extra linens, shampoo and soap
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$4,876
for 7 nights, 1 home
AU$697 per night
includes taxes & fees
Victorian Village Home in Town! with access to shuttle service to Okemo.
Light filled kitchen
Front of house, early spring
Bedroom #2 Queen bed with large windows & french doors
Open living room with french doors, huge windows & vaulted ceiling
Exceptional
(5 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
AU$5,881
for 7 nights, 1 home
AU$840 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Exterior
Kitchen with 2 DW, Stove and Wall oven, Micro. 5 seats at island, 3 seats at bar
Property grounds
1st Floor Living Room with Sectional, SMART TV and Gas Fireplace.
Exceptional
(6 reviews)

STAY WITH US, Brand New, 8 BR, 4 Bth, 1/2 mi to Okemo, Hot Tub, on Shuttle, King

Ludlow

12% off
AU$10,810
for 7 nights, 1 home
AU$1,544 per night
includes taxes & fees
STAY WITH US, Brand New, 8 BR, 4 Bth, 1/2 mi to Okemo, Hot Tub, on Shuttle, King
Queen
Hot Tub
2nd Living Room with Fireplace and Flat Screen TV
Dining
Exceptional
(85 reviews)

Fabulous 10 BR, 5 Bath, 5 min to OKEMO Mtn, on Shuttle Rte, Hot Tub, King

Ludlow

12% off
AU$13,888
for 7 nights, 1 home
AU$1,984 per night
includes taxes & fees
Fabulous 10 BR, 5 Bath, 5 min to OKEMO Mtn, on Shuttle Rte, Hot Tub, King
Dining
Pool in the nearby recreational building
Living area
Living area
Exceptional
(139 reviews)

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

Ludlow

8% off
AU$3,697
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace
Take a seat by the fireplace with bookshelves and media storage close at hand.
Enjoy a warm soak on the covered deck with the mountain rising beyond the neighborhood.
A flower-lined walkway leads to the clubhouse entrance through mature green landscaping.
Tall windows fill the indoor pool room with daylight and views of the surrounding greenery.
Exceptional
(70 reviews)

Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals

Killington

15% off
AU$9,298
for 7 nights, 1 apartment
AU$1,328 per night
includes taxes & fees
Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals
Room
Private kitchen
Living area
Property grounds
Exceptional
(17 reviews)

Updated Main St Condo in downtown Ludlow!

Ludlow

12% off
AU$1,539
for 7 nights, 1 apartment
AU$220 per night
includes taxes & fees
Updated Main St Condo in downtown Ludlow!
Interior
Property grounds
Dining
Living area
Exceptional
(14 reviews)

Okemo Mountain Ski-In/ski-out Condo Overlooking Kettlebrook Trail

Ludlow

8% off
AU$14,392
for 7 nights, 1 apartment
AU$2,056 per night
includes taxes & fees
Okemo Mountain Ski-In/ski-out Condo Overlooking Kettlebrook Trail
Living area
Dining
Private kitchen
Property grounds
Exceptional
(13 reviews)

Cozy Rutland Retreat

Rutland

8% off
AU$1,651
for 7 nights, 1 apartment
AU$236 per night
includes taxes & fees
Cozy Rutland Retreat
Dining
Interior
Exterior
Private kitchen
Exceptional
(11 reviews)

Main St Studio - Newly Updated!

Ludlow

8% off
AU$1,450
for 7 nights, 1 apartment
AU$207 per night
includes taxes & fees
Main St Studio - Newly Updated!
view of trail from the street in front of condo
Exterior
Eat in kitchen
Mud room with Ski Closet
Exceptional
(34 reviews)

OKEMO Trailside Ski Condo, Walk to Sachem Trail, Sleeps 8

Ludlow

8% off
AU$14,539
for 7 nights, 1 apartment
AU$2,077 per night
includes taxes & fees
OKEMO Trailside Ski Condo, Walk to Sachem Trail, Sleeps 8
Property grounds
Outdoor dining
Exterior
Interior
Exceptional
(5 reviews)

Serene apartment in Dorset perfect for a relaxing getaway

Dorset

8% off
AU$1,367
for 7 nights, 1 apartment
AU$195 per night
includes taxes & fees
Serene apartment in Dorset perfect for a relaxing getaway
Living room with mountain valley view.
Fire place at living room.
Dining area.
The living room.
Exceptional
(46 reviews)

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Ludlow

8% off
AU$3,855
for 7 nights, 1 apartment
AU$551 per night
includes taxes & fees
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Main room facing northwest
Terrace/patio
Main room facing north.
The Shepherds' Cabin
Exceptional
(104 reviews)

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow

12% off
AU$3,788
for 7 nights, 1 cabin
AU$541 per night
includes taxes & fees
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Dining
Private kitchen
Private kitchen
Exterior detail
Exceptional
(100 reviews)

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

Mount Holly

8% off
AU$3,006
for 7 nights, 1 cabin
AU$429 per night
includes taxes & fees
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
X-Large Kitchen
Exterior
Interior
Interior
Exceptional
(18 reviews)

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

Dorset

16% off
AU$4,593
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Exterior
Property grounds
Dining
Interior
Exceptional
(9 reviews)

Winterplace E building - top of the Quad

Ludlow

8% off
AU$6,027
for 7 nights, 1 apartment
AU$861 per night
includes taxes & fees
Winterplace E building - top of the Quad

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Book a holiday rental for your Wallingford getaway

Learn about the unique charm of Wallingford with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Wallingford

Are you hoping to discover attractions to see in the city? Venture out of your holiday home and experience everything that makes Wallingford a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Pond Hill Ranch and Pro Rodeo (11.5 mi / 18.5 km)
  • Okemo Mountain Resort (13.9 mi / 22.4 km)
  • Killington Resort (14.1 mi / 22.6 km)
  • Pico Mountain at Killington Ski Resort (14.1 mi / 22.7 km)
  • Killington Golf Course (14.2 mi / 22.8 km)
  • Green Mountain National Golf Course (17.2 mi / 27.6 km)

Exploring the natural features in Wallingford

Whether you're an adventurous traveller or just want to appreciate the scenery, Wallingford is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Green Mountain National Forest (11.7 mi / 18.8 km)
  • Lake Saint Catherine (11.9 mi / 19.2 km)
  • Killington Peak (12.1 mi / 19.5 km)
  • Buttermilk Falls (12.6 mi / 20.4 km)
  • Emerald Lake State Park (13.2 mi / 21.3 km)
  • Pico Peak (13.6 mi / 21.8 km)

Transport to and around Wallingford

The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 4.2 mi (6.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Springfield, VT (VSF-Hartness State), which is 24.5 mi (39.4 km) away.

Frequently asked questions

What is the best area to stay in Wallingford when booking a holiday rental?
When considering a holiday rental in Wallingford, Vermont, the areas surrounding the town centre are particularly appealing. The charming community offers a picturesque New England setting, characterised by its historic buildings and scenic landscapes. Here, visitors can find a variety of properties, ranging from quaint cottages to more spacious family homes, making it an ideal choice for different group sizes and preferences.One great attraction nearby is the Green Mountain National Forest, which provides ample opportunities for outdoor activities such as hiking, biking, and enjoying the stunning fall foliage. Additionally, the picturesque Lake Bomoseen is just a short drive away, superb for those looking to engage in water sports or simply relax by the shore.Staying in Wallingford ensures easy access to these natural wonders while allowing guests to experience the warmth of a small-town atmosphere.
Where are the best areas for renting a beach house in Wallingford?
For renting a beach house in Wallingford, Vermont, potential travellers should head towards the nearby Lake Bomoseen area, which offers a picturesque setting and a variety of rental options along the lakefront. Here, visitors can find charming cottages and homes that typically feature amenities such as private docks, outdoor patios, and fully equipped kitchens, ideal for families or groups looking to enjoy a lakeside retreat.The properties in this area often provide easy access to the water for swimming, fishing, and boating, with some rentals offering kayaks or paddleboards as part of the package. Lake Bomoseen State Park, located not far from the rentals, is a great spot for hiking and picnicking, further enhancing the outdoor experience.Additionally, the surrounding countryside boasts beautiful views and opportunities for hiking, especially in the nearby Green Mountain National Forest, where trails cater to various skill levels and provide stunning vistas.
Where are the best Wallingford ski resort rentals?
For skiing near Wallingford, Vermont, the closest major ski area is Okemo Mountain Resort, located just a short drive away. Travellers looking for ski resort rentals should consider the charming town of Ludlow, which is conveniently situated near Okemo. In Ludlow, you'll find a variety of rental properties, including cosy chalets and spacious condos, many of which come equipped with amenities such as full kitchens, fireplaces, hot tubs, and ski storage, superb for unwinding after a day on the slopes.Additionally, the area around Wallingford offers rustic farmhouse rentals and quaint cabins that provide a more secluded experience, allowing guests to enjoy the serene Vermont countryside. These properties often feature outdoor spaces with stunning mountain views, fire pits for evening gatherings, and proximity to local trails for winter hiking or snowshoeing.For those seeking a vibrant après-ski scene, Ludlow boasts a selection of local restaurants and shops, making it easy to enjoy the local culture.
What is the most popular type of holiday rental accomodation in Wallingford?
In Wallingford, holiday houses are the most popular holiday rental option, with around 12 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Additionally, there are several cottages and cabins that offer a charming and rustic experience, often located in scenic settings. These properties usually come with cozy living areas and outdoor spaces for relaxing amid nature.
Are there any family house rentals in Wallingford?
In Wallingford, Vermont, there are several family-friendly house rentals available, making it a wonderful destination for those travelling with children. The area boasts spacious properties that often come equipped with amenities such as full kitchens, allowing families to prepare meals together after a day of exploration. Many homes feature outdoor spaces where kids can play, such as gardens or yards, and some may even include entertainment options like game rooms or recreational equipment.Visitors to Wallingford can enjoy the scenic beauty of the surrounding Green Mountains, which provide ample opportunities for outdoor activities like hiking, biking, and in winter, skiing at nearby resorts. The charming downtown area offers local shops and restaurants, adding to the community feel of this delightful locale.
Can I rent a holiday home with a pool or hot tub in Wallingford?
In Wallingford, Vermont, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers looking to relax and unwind. The area boasts a picturesque setting with easy access to outdoor activities, including hiking and skiing during the winter months. Many of these properties come equipped with amenities like private pools, hot tubs, outdoor decks, and spacious living areas, great for families or groups seeking comfort and leisure. Additionally, fully equipped kitchens are common, allowing guests to prepare meals while enjoying the scenic surroundings.
Are there pet-friendly house rentals in Wallingford?
In Wallingford, there are several pet-friendly house rentals available, making it an inviting destination for those travelling with their furry companions. Many of these holiday homes come equipped with amenities such as fully stocked kitchens, spacious living areas, and private outdoor spaces where pets can roam freely. Additionally, some properties may feature features like fenced yards or proximity to walking trails, providing ample opportunities for exercise and exploration.The surrounding area offers charming rural landscapes, and nearby attractions include the scenic Green Mountain National Forest, which features numerous trails suitable for hiking with pets. Wallingford itself provides a quaint atmosphere, with local shops and eateries that may welcome pets, ensuring a pleasant experience for both travellers and their pets.
Are there any remote work holiday rentals in Wallingford?
In Wallingford, Vermont, there are approximately 18 holiday rentals suitable for remote work. This charming town offers a peaceful setting, ideal for those needing to balance work and leisure. Many of these properties come equipped with high-speed internet and Wi-Fi, ensuring that guests can stay connected while enjoying the serene surroundings.Accommodations often feature comfortable workspaces, allowing for productive days, and some may include additional amenities such as well-equipped kitchens for home-cooked meals and cozy living areas for relaxation after work. The picturesque landscapes and local attractions, such as nearby hiking trails and quaint shops, provide ample opportunities for unwinding during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Wallingford?
In Wallingford, popular rental amenities include kitchens, allowing guests to prepare their own meals, and fireplaces that create a warm and inviting atmosphere. Many rentals also feature coffee and tea makers for a convenient morning brew. Outdoor spaces such as decks or patios are common, providing a lovely area to relax and enjoy the surrounding scenery. Additionally, onsite parking is typically available, making it easy for visitors to explore the area and nearby attractions.
When is the best time to visit Wallingford for a holiday rental?
The peak travel season for Wallingford runs from July to September, making it the most popular time for holiday rentals. During these months, visitors flock to the area to enjoy the lush green landscapes and partake in a variety of outdoor activities, such as hiking and cycling, which are superb for those seeking adventure amidst nature. The warm summer temperatures, typically ranging from the low 20s to mid-30s Celsius, create an inclusive setting for exploration and relaxation.July stands out as the prime month to experience Wallingford, with vibrant local events, farmers' markets, and the chance to immerse yourself in the region's charming community spirit. The pleasant weather makes it ideal for outdoor sightseeing, whether you're strolling through picturesque streets or enjoying nearby parks and lakes.If you're looking for a more budget-friendly option, consider visiting in December. While this month falls outside the peak season, it offers a great experience with the winter wonderland aesthetics and opportunities for snow-related activities. The tranquil ambiance in Wallingford during this time allows for a peaceful retreat, superb for those who appreciate a quieter getaway.
What are the top attractions in Wallingford?
In Wallingford, Vermont, visitors can enjoy a charming blend of natural beauty and local culture. The area is known for its picturesque landscapes, with opportunities for outdoor activities such as hiking and fishing in the nearby Green Mountain National Forest. The quaint downtown area features local shops and eateries, providing a taste of community life.Just a short drive away, the historic town of Rutland offers additional attractions, including the Paramount Theatre and various art galleries. For those interested in winter sports, the nearby Killington Resort is accessible for skiing and snowboarding enthusiasts.
Are all fees included in the Wallingford 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 Wallingford holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wallingford 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 Wallingford holiday homes?
You can find great discounts on holiday homes in Wallingford 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 Wallingford holiday home booking on Stayz?
To find Wallingford 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 Wallingford?
A long-stay holiday home in Wallingford 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 Wallingford holiday home?
Book your Wallingford 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 Wallingford?
Prices for holiday homes in Wallingford 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 Wallingford 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.