Londonderry vacation rentals

We found 1,611 vacation rentals — enter your dates for availability

Nestled in the heart of Vermont, Londonderry beckons with its stunning landscapes, serene state parks, and world-class winter sports at nearby Killington Resort. This charming destination offers a perfect blend of outdoor adventures, from hiking and fishing to skiing, catering to groups and families alike. With cozy cabins and spacious vacation homes that provide all the comforts of home, your stay in Londonderry promises a rejuvenating escape filled with unforgettable experiences and lasting memories.

Holiday rentals with weekly discounts - Londonderry

Showing deals for:Dec 11 - Dec 18

Exterior
Property grounds
Dining
Living area
Exceptional
(48 reviews)

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

Ludlow

9% off
$807
$5,651 for 7 nights
All fees included
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Interior
Another view of the front of the home and the front porch in the summer.
Basement bedroom with 2 bunk beds, sleeps 4
The back deck with outdoor dining for 12 in the summer. A very private property.
Exceptional
(96 reviews)

Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12

Ludlow

17% off
$702
$4,914 for 7 nights
All fees included
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
Interior
Exterior
Exterior
Private kitchen
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

9% off
$2,922
$20,455 for 7 nights
All fees included
Beautiful Lakeview Log Cabin on 60-Acre Property
Outdoor dining
Interior
Enjoy a nice fire while you overlook the Sachem Trail and watch people ski by.
Private kitchen
Exceptional
(32 reviews)

Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults

Ludlow

9% off
$2,058
$14,406 for 7 nights
All fees included
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
Interior
Living area
Room
Private kitchen
Exceptional
(16 reviews)

Okemo Mountain View Retreat

Cavendish

9% off
$944
$6,606 for 7 nights
All fees included
Okemo Mountain View Retreat
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)

September & October available! Luxury 9BRs Stratton Estate. Pool, Mountain Views

Bondville

9% off
$2,461
$17,227 for 7 nights
All fees included
September & October available! Luxury 9BRs Stratton Estate. Pool, Mountain Views
Living area
Living area
Interior
Interior
Exceptional
(12 reviews)

Forest Lodge - Near 6 Ski Resorts

Jamaica

9% off
$1,106
$7,742 for 7 nights
All fees included
Forest Lodge - Near 6 Ski Resorts
Dining room
Living area
Back porch
Front door
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
$336
$2,349 for 7 nights
All fees included
Wishing Well Cabin
View of the Main house living room from the kitchen bar
Main house top floor river room with sounds of the river out the windows.
2nd - 3rd floor main house stairs
Main house top floor river room with deck overlooking the pool and backyard.
Exceptional
(38 reviews)

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

Wardsboro

9% off
$2,063
$14,442 for 7 nights
All fees included
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Living area
Living area
Outdoor dining
Master bedroom to the left of kitchen. Entryway and den to the right.
Exceptional
(113 reviews)

Spacious, Comfortable & Close!!! GOLF TRIPS!

West Dover

16% off
$734
$5,139 for 7 nights
All fees included
Spacious, Comfortable & Close!!! GOLF TRIPS!
Living room. New smart TV. Dining area
New living room furniture January of 2026. Sectional sofa. Smart TV.
Solitude recreation center. Indoor /outdoor pool and hot tub. We are walk to it
Bedroom 1- King bed with private large bathroom attached
Exceptional
(27 reviews)

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

Ludlow

9% off
$1,406
$9,844 for 7 nights
All fees included
A1 Solitude.4 BDRM, ski in/out to main Solitude lift, pool/gym access. Parking!
Terrace/patio
Large open-concept living and kitchen area
3-Season porch (new addition 2023)
Dining area
Exceptional
(18 reviews)

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

Wardsboro

8% off
$509
$3,562 for 7 nights
All fees included
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Room
Interior
Dining
Private kitchen
Exceptional
(78 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

21% off
$933
$6,533 for 7 nights
All fees included
Western Mountain Lodge on River and Close to Stratton
Indoor pool in Winterplace clubhouse building
New kitchen and appliances which opens to living room
Master bedroom with full private bath and private balcony
Summer golf at Okemo Valley Golf club which is spectacular!
Exceptional
(40 reviews)

Okemo Winterplace - Ski home for lunch-Sleeps 12 people 4Br 2BA slopeside

Ludlow

5% off
$3,086
$21,599 for 7 nights
All fees included
Okemo Winterplace - Ski home for lunch-Sleeps 12 people 4Br 2BA slopeside
Private kitchen
Living area
Open free form decks
Extensive glass overlooking deck & pond
Exceptional
(255 reviews)

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Bondville

8% off
$230
$1,613 for 7 nights
All fees included
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Interior
Interior
Dining
Private kitchen
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

9% off
$1,352
$9,465 for 7 nights
All fees included
Skylight Ski Lodge VT Rustic Chic Near Stratton
Outdoor spa tub
One of a kind woodwork, beautiful handmade furniture and built ins.....
The tile work in all bathrooms and kitchen are unique hand made tiles
Master bedroom is 12X20 and overlooks our beautiful river - private bathroom
Exceptional
(53 reviews)

One of a Kind Post and Beam Home on Private 100 acre Island

Jamaica

8% off
$863
$6,042 for 7 nights
All fees included
One of a Kind Post and Beam Home on Private 100 acre Island
The formal dining room adjacent to the smaller dining room. Seating for 14 or more if you're strategic!
Outdoor spa tub
Another one of the living spaces with a 60" smart TV for you to sign into all the things. Ample space around the house for everyone to be comfortable.
The twin bed with our ski mountain mural with the pink moon. While this room does not have it's own private. bath, it's the perfect room for the kids, 1/2 bath right outside the door in the hallway and a full bath at the end of the hallway would be for this room.
Exceptional
(7 reviews)

$0 Fees 7 Bdrms 9 Bthrms Minutes to Okemo Hot Tub

Cavendish

14% off
$1,002
$7,015 for 7 nights
All fees included
$0 Fees 7 Bdrms 9 Bthrms Minutes to Okemo Hot Tub
Private driveway with ramp to enter house. Gently babbling stream in the front
Front of house, early spring
Light filled kitchen
Open living room with french doors, huge windows & vaulted ceiling
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

9% off
$543
$3,802 for 7 nights
All fees included
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Interior
Terrace/patio
Exterior
Interior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

9% off
$939
$6,574 for 7 nights
All fees included
Modern mountain home - Vermont Ski House close to Stratton
Private kitchen
Interior
Interior
Exterior
Exceptional
(7 reviews)

Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!

Bondville

9% off
$2,314
$16,199 for 7 nights
All fees included
Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!
let it snow!
Outdoor dining
living room
main entrance
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

8% off
$448
$3,135 for 7 nights
All fees included
Cozy Manchester Getaway with Amazing Views!!!
Exterior
Property grounds
Private kitchen
Room
Exceptional
(27 reviews)

Bear Pass Bunkhouse

Manchester

9% off
$285
$1,995 for 7 nights
All fees included
Bear Pass Bunkhouse
Kitchen Island
Hot Tub
2nd Living Room with Fireplace and Flat Screen TV
Queen
Exceptional
(85 reviews)

Sleeps 30 - 10BR - 5 Min to Okemo - Hot Tub - Walk to Downtown Ludlow

Ludlow

13% off
$1,079
$7,555 for 7 nights
All fees included
Sleeps 30 - 10BR - 5 Min to Okemo - Hot Tub - Walk to Downtown Ludlow
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Londonderry

Why visit Londonderry

  • Outdoor Adventure: Londonderry is a haven for adventure seekers, offering skiing, hiking, and breathtaking national parks.
  • Picturesque Waterfalls: Explore stunning waterfalls that provide scenic views and perfect photo opportunities.
  • Cozy Accommodations: Choose from a variety of vacation rentals, including charming cabins and modern condos, tailored to your needs.
  • Family-Friendly Activities: Enjoy a lively atmosphere with activities perfect for families and ski enthusiasts alike.
  • Welcoming Community: Experience the warmth and camaraderie of the friendly locals that make Londonderry special.

Popular types of accommodation in Londonderry

Planning a getaway to Londonderry? Discover an array of vacation rentals perfect for your needs, from cozy private homes and modern condos to charming cabins. Whether you’re searching for pet-friendly options or looking to save on your stay, our platform has you covered. Explore the best Londonderry vacation rentals for a memorable Vermont experience.

  • Houses: These are the top choice for visitors to Londonderry, offering spacious and comfortable accommodations perfect for families or groups seeking a home-like experience.
  • Condos: A popular option for those wanting a blend of convenience and luxury, condos provide modern amenities and often stunning views.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic escape with a cozy atmosphere amidst beautiful landscapes.
  • Cottages: These quaint and charming rentals provide a perfect retreat for couples or solo travelers looking for a peaceful getaway.
  • Apartments: A versatile option for solo travelers or small groups, apartments offer accessible living spaces in the heart of Londonderry.**

Top attractions in and around Londonderry

Londonderry, Vermont, is an ideal destination for ski enthusiasts and adventure seekers, offering a variety of outdoor activities and cultural experiences. Visitors can explore stunning national parks, enjoy thrilling days at ski resorts, and marvel at picturesque waterfalls, making it a perfect spot for an exciting vacation filled with nature and adventure.

  • Stratton Mountain Resort: Experience thrilling skiing and snowboarding on diverse terrain. In the warmer months, enjoy hiking, mountain biking, and stunning outdoor vistas, making it a year-round adventure hub.
  • Lowell Lake State Park: Embrace nature with serene hiking trails, picturesque views, and the tranquil beauty of Lowell Lake. Perfect for picnicking, fishing, and exploring the lush landscape.
  • Stratton Tennis School: Dive into a cultural experience with expert tennis education. Enjoy lessons in a friendly environment, enhancing your skills while soaking up the vibrant community spirit.

Things to do recommended for couples

For a romantic getaway in Londonderry, embrace the thrill of skiing at Magic Mountain Ski Resort or Stratton Mountain Resort, just 10 miles away. Enjoy the adventure at the American Express Ski Lift, located 9 miles from town. Experience the perfect blend of romance and outdoor fun.

Things to do recommended for families

Families visiting Londonderry can have a thrilling time at the Bromley Alpine Slide, just 7 miles away. For relaxation, head to Dana L. Thompson Memorial Park, 13 miles away, or enjoy ice skating at The Ice House, located 14 miles from Londonderry.

Things to do recommended for groups

Your group can enjoy a theatrical performance at the Weston Playhouse, just 5 miles from Londonderry, explore the local flavors at the West River Farmers Market, or tee off at the scenic Stratton Mountain Golf Course, located 4 miles away, for an unforgettable outdoor experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Londonderry

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your preferences during the booking process. Here are some helpful Vrbo tips to assist you.

  • Traveling to Londonderry with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Londonderry with young kids: Traveling with young kids can be tough. It's important to keep their comfort and safety in mind, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Londonderry: For many families, a vacation wouldn't feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer amenities like food bowls and beds to ensure that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Londonderry: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Londonderry

Discover the charm of Londonderry, Vermont, where adventure meets relaxation. Perfect for ski enthusiasts and families alike, this friendly town offers a lively atmosphere filled with camaraderie. Explore nearby destinations showcasing stunning scenery and romantic spots, making it an ideal getaway for all. Whether you seek thrilling outdoor sports or cozy family outings, Londonderry promises an unforgettable experience infused with the warmth of its welcoming community.

  • Weston: Nestled a mere 5 miles from Londonderry, Weston is a charming city known for its breathtaking landscapes and outdoor adventures. This destination is perfect for ski enthusiasts, with easy access to several ski fields and resorts. Beyond winter sports, Weston offers stunning views of nearby lakes, valleys, and mountains, making it an ideal spot for hiking and nature walks during warmer months. Don't miss a visit to the Weston Playhouse Theatre, where you can enjoy local performances in a quaint setting.
  • Manchester Center: Located 13 miles from Londonderry, Manchester Center is a vibrant hub for travelers seeking adventure and sports. This city is renowned for its ski facilities and is surrounded by beautiful lakes and mountains, providing ample opportunities for outdoor activities year-round. Shopping enthusiasts will appreciate the variety of boutiques and outlets in the area, while the picturesque scenery offers perfect backdrops for photography. Be sure to explore the local dining scene, which features a range of options from cozy cafes to upscale restaurants.
  • Ludlow: Also situated 13 miles from Londonderry, Ludlow is a picturesque city that attracts adventure seekers and ski lovers alike. With its proximity to ski resorts, it’s an excellent base for winter sports. In addition to skiing, Ludlow provides opportunities for hiking and exploring the surrounding natural beauty, characterized by stunning lakes, mountains, and valleys. The city's charming downtown area features locally-owned shops and eateries, making it a delightful spot to unwind after a day of adventure.

Best time to go to Londonderry

If you're planning a trip to Londonderry, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in January, July and September, while off-peak times, like April to May and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.8°F (-6.8°C)Light RainMostly CloudySlightly HighSlightly High
February21.7°F (-5.7°C)Light RainMostly CloudyAverageSlightly High
March29.7°F (-1.3°C)Light RainMostly CloudyAverageAverage
April41.9°F (5.5°C)Light RainMostly CloudySlightly LowSlightly Low
May54.9°F (12.7°C)Light RainMostly SunnySlightly LowSlightly Low
June62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
July68.2°F (20.1°C)Light RainMostly SunnySlightly HighAverage
August66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
September59.4°F (15.2°C)Light RainMostly SunnySlightly HighSlightly Low
October47.8°F (8.8°C)Light RainMostly CloudyAverageAverage
November35.4°F (1.9°C)Light RainMostly SunnySlightly LowAverage
December26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can start new trips, continue from where you last stopped, or manage your existing plans all in one place. Your saved or booked properties will be neatly organized under categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the majestic setting in Londonderry

The mountains and countryside provide a pleasant backdrop to your vacation home in Londonderry. Well known for its skiing, bars and coffeehouses, this welcoming city won't disappoint. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Londonderry

Are you hoping to find things to do in the city? Venture out of your vacation home and experience everything that Londonderry has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Viking Nordic Center (1.1 mi / 1.8 km)
  • Magic Mountain Ski Resort (3 mi / 4.8 km)
  • Jamaica State Park (5.5 mi / 8.9 km)
  • Bromley Mountain Ski Resort (6.6 mi / 10.7 km)
  • Stratton Mountain Golf Course (8.5 mi / 13.8 km)
  • Stratton Mountain Resort (10.1 mi / 16.3 km)

Exploring the natural features in Londonderry

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Londonderry. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Lowell Lake State Park (2.1 mi / 3.3 km)
  • Winhall River (5.8 mi / 9.3 km)
  • Emerald Lake State Park (10.7 mi / 17.2 km)
  • Green Mountain National Forest (11.4 mi / 18.4 km)
  • Battenkill River (12.8 mi / 20.6 km)
  • Equinox Preservation Trust (14.9 mi / 23.9 km)

Seasonal weather in Londonderry

Travelers enjoy Londonderry for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, February or December, when snowfall averages 8 inches and temperatures average 24°F.

Traveling to and around Londonderry

The nearest airport is in Springfield, VT (VSF-Hartness State), located 16.4 mi (26.4 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 22 mi (35.3 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Londonderry?
Based on our research, chalets are the most in-demand type of vacation rental in Londonderry. But of course, everyone's idea of an awesome trip can differ. Vrbo has vacation rentals in a variety of sizes and shapes, and we'll help you find your perfect match.
How much does it cost to rent a vacation rental in Londonderry?
The average price for a vacation home in Londonderry is determined by a number of factors, including property type, length of stay and time of year. Whether you're in search of a villa with space for extended family or a cozy condo that's perfect for two, just add your dates of travel to view some great-value stays.
How much does it cost to rent a beach house in Londonderry?
When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Type in your Londonderry travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use our filters to select the amenities and features you need.
Are there pet-friendly vacation rentals in Londonderry?
Yes, there are. Pick from 68 vacation rentals that welcome pets in Londonderry on Vrbo. Our furry friends also need a break, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where your pooch can lap up the good times.
Can I rent a house with a pool in Londonderry?
Dig out your swimsuit and inflatable flamingo, because there are 13 houses with a private pool in Londonderry. Settle in at one of these superb vacation rentals and let every day be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Londonderry?
A sauna, a barbecue grill and a nearby river head the list of most popular rental amenities in Londonderry. Whether you're taking a trip on your own, with your significant other or a group of friends, Vrbo can help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Londonderry?
You can choose from 29 properties in Londonderry that can sleep 10 or more people. Whether you're planning a get-together with extended family or a special event like a birthday party, there's plenty of space to get your loved ones together under the same roof.
Are there vacation rentals in Londonderry that welcome kids?
Gather your entire family for a fun-filled adventure in Londonderry at one of our 67 family-friendly vacation homes. Many of these stays come with amenities that are ideally suited to getaways with children, including dining rooms, bunk beds and private pools. Simply check the "Properties good for families" filter box and decide on your favorite.
What are the top attractions for families in Londonderry?
Keep the kids entertained at these fabulous family-friendly attractions in Londonderry:
  • Taylor Farm
  • Viking Nordic Center
  • Lowell Lake State Park
Are there one-bedroom vacation rentals in Londonderry?
Londonderry has eight one-bedroom rentals on offer. Often situated in prime spots due to their smaller size, a one-bedroom vacation rental is ideal if you're getting away with a buddy or your partner. And with plenty of home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this terrific destination.
Can I find two-bedroom vacation rentals in Londonderry?
Select from six two-bedroom homes in Londonderry. Put your little ones in the second room or maybe fill it with a couple of your besties. There's enough space for whoever's fortunate enough to be joining your adventure.
Are there vacation rentals with WiFi in Londonderry?
Whether you'd like to keep up with world events, look over emails or surf social networks, there are 27 vacation homes with WiFi in Londonderry. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Londonderry?
Work out your travel dates and then make use of the filters to see vacation rentals with ac in Londonderry on Vrbo. With 26 air-conditioned properties available here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a vacation rental in Londonderry?
The minimum age permitted can differ across properties on Vrbo, so check the rules of the vacation rental in Londonderry you're considering. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Londonderry for?
The amount of time you can rent a Londonderry vacation rental for is up to each property. Simply enter your preferred travel dates to view options offering longer term stays. They feature all the things you need to make your extended trip more enjoyable and comfortable, such as kitchens and backyards. Some vacation homes might also offer weekly or monthly discounted prices, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Londonderry?
Weekend retreat or a much-needed extended vacation, Vrbo has some exclusive deals and discounted options in Londonderry that'll suit your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what's just been added with one of our newly listed homes. Whatever it is you're after, you'll find the ideal place to stay — without spending a fortune.

More Vacation Ideas