Rutland holiday lettings

We found 2,197 holiday rentals — enter your dates for availability

Select from 46 houses, 17 flats and other holiday rentals to find the perfect place for your stay in Rutland. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as 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 - Rutland

Showing deals for:13 Mar - 20 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

8% off
Price is £3,231
for 7 nights, 1 chalet
£462 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Find spaces that suit your style

Why visit Rutland

  • Outdoor Adventure: Rutland is a haven for skiing and adventure sports enthusiasts, with excellent ski resorts and outdoor activities.
  • Scenic Beauty: Enjoy picturesque lakes and stunning state parks that offer breathtaking views and recreational options.
  • Charming Atmosphere: Experience the friendly community and vibrant culture that make Rutland an inviting destination.
  • Diverse Accommodation: Choose from a variety of lodging options, including private vacation homes, cabins, and stylish studios.
  • Family-Friendly Activities: Rutland caters to families with a range of engaging activities suitable for all ages.

Popular types of accommodation in Rutland

Planning a getaway to Rutland? The charm of this picturesque destination awaits you, and selecting the perfect accommodation is key. Explore an array of popular options such as houses, condos, and cosy cabins. Whether you’re looking for long-term stays, stylish studios, or meeting room hire, Rutland has something to suit every traveller's needs. Discover the ideal bed apartment for your next adventure with us!

  • Houses: The top choice for visitors to Rutland, these homes offer spacious and comfortable accommodations ideal for families or groups.
  • Condos: A popular option for those seeking modern amenities, condos provide a convenient and stylish base for exploring the area.
  • Cabins: Perfect for nature enthusiasts, these rustic retreats offer a serene escape amidst beautiful surroundings.
  • Cottages: Our charming cottages provide a quaint and cosy atmosphere for a delightful stay.
  • Apartments: These versatile spaces are great for couples or solo travellers, offering a practical home-away-from-home experience.**

Top attractions in and around Rutland

Rutland, Vermont, is an ideal destination for skiing and adventure sports enthusiasts. With a variety of attractions such as ski resorts, picturesque lakes, and stunning state parks, it offers a wealth of outdoor activities perfect for families and thrill-seekers alike. Whether you're seeking an exhilarating adventure or a relaxing family experience, Rutland has something to delight every traveller.

  • Vermont State Fairgrounds: A vibrant fairground located in Rutland, perfect for family outings. Enjoy various events, exhibitions, and the lively atmosphere that embodies the spirit of Vermont.
  • Wilson Castle: A stunning historic manor just 1.2km from Rutland, showcasing exquisite architecture and rich cultural heritage. Wander through its elegant rooms and enjoy the picturesque grounds.
  • McLaughlin Falls: A beautiful waterfall nestled within Rutland, ideal for outdoor adventures. Experience the enchantment of nature, perfect for a romantic stroll or a thrilling hike.

Things to do recommended for couples

For a romantic getaway in Rutland, embrace the thrills at Pico Mountain and Pico Peak, both a mere 5.0km away, perfect for skiing and outdoor adventures. Don't miss the stunning views from the K-1 Express Gondola, located 5.6km from Rutland, for a truly unforgettable experience.

Things to do recommended for families

Your family will have a fantastic time in Rutland, exploring the Green Mountain Rock Climbing Center for adventure, relaxing at Pine Hill Park, and experiencing the thrilling Timber Ripper Mountain Coaster, located 11.2km away. These activities promise fun and excitement for all ages!

Things to do recommended for groups

Groups visiting Rutland can enjoy a captivating performance at the Paramount Theater, relax at the scenic Rutland Country Club for a round of golf, or indulge in shopping and entertainment at the Diamond Run Mall, providing a perfect blend of culture, sports, and leisure activities.

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

If you’re travelling with a group, as a family, bringing your pets, or seeking longer stays, be sure to refine your search based on your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Rutland with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Rutland with young kids: Embarking on a journey with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to take into account how close you are to attractions that are suitable for families.
  • Taking your pets with you to Rutland: For many, a family holiday isn’t truly fulfilling unless their four-legged companion is part of the adventure. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortably at home.
  • Planning for a long term stay visiting Rutland: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private swimming pool in your search criteria.

Where to stay in and around Rutland

Rutland, Vermont offers a delightful blend of adventure and charm, perfect for ski enthusiasts and families alike. Explore the scenic beauty and friendly atmosphere of this vibrant city, while nearby destinations like Uppingham and Central London provide a romantic and historical backdrop. With stunning views, recreational activities, and a welcoming community, your stay in Rutland promises to be both enjoyable and memorable.

  • Killington: Situated approximately 6.8km from Rutland, Killington is renowned for its vibrant ski culture and adventure sports. This city is a magnet for thrill-seekers and outdoor enthusiasts, offering a range of activities including skiing and snowboarding at its famous ski resort. The idyllic landscape features stunning mountains, serene lakes, and picturesque valleys, making it an ideal backdrop for both winter sports and summertime hiking. Killington is not merely a ski destination; it also boasts charming local eateries and lively après-ski options, creating a well-rounded travel experience.
  • Mendon: Nestled in the vicinity of Rutland, Mendon is a quaint village that appeals to those seeking a blend of relaxation and adventure. Visitors are drawn here for its skiing opportunities and outdoor activities, with easy access to ski fields and resorts. The village is enveloped by beautiful lakes and majestic mountains, providing ample opportunities for exploration and photography. Mendon’s charming atmosphere, coupled with its stunning natural beauty, makes it a delightful stop for tourists looking to unwind after a day on the slopes.
  • Clarendon: Just 1.9km from Rutland, Clarendon is a tranquil village that offers an inviting escape for outdoor lovers. With its proximity to ski fields and resorts, Clarendon is a prime location for skiing and winter sports. The village is surrounded by scenic lakes and valleys, alongside the nearby national state park, which presents opportunities for hiking and wildlife observation. Clarendon is an excellent choice for those looking to experience Vermont's natural splendour while enjoying a peaceful village atmosphere.

Best time to go to Rutland

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.1°F (-6.6°C)Light RainMostly CloudyAverageSlightly High
February22.3°F (-5.4°C)Light RainMostly CloudyAverageSlightly High
March30.6°F (-0.8°C)Light RainMostly CloudySlightly HighAverage
April43.0°F (6.1°C)Light RainMostly CloudyAverageSlightly Low
May56.1°F (13.4°C)Light RainMostly SunnySlightly LowSlightly Low
June63.5°F (17.5°C)Light RainMostly SunnyAverageAverage
July69.4°F (20.8°C)Light RainMostly SunnySlightly HighAverage
August67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
September60.4°F (15.8°C)Light RainMostly SunnySlightly HighSlightly Low
October48.9°F (9.4°C)Light RainMostly CloudyAverageAverage
November36.1°F (2.3°C)Light RainMostly CloudySlightly LowAverage
December27.5°F (-2.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a dedicated area for you to plan new trips, keep your arrangements on track, or manage your existing bookings. The properties you've saved or reserved are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting scenic Rutland

The mountains and waterfalls create a pretty picture of Rutland. This scenic and welcoming city is well known for its skiing, shopping and restaurants. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Rutland

Do you want to discover things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Rutland a fun place to get away to. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Pico Mountain at Killington Ski Resort (7.6 mi / 12.2 km)
  • Pond Hill Ranch and Pro Rodeo (9.1 mi / 14.6 km)
  • Killington Adventure Center (9.3 mi / 14.9 km)
  • Killington Resort (9.3 mi / 15 km)
  • Killington Golf Course (9.4 mi / 15.2 km)
  • Green Mountain Sugar House (18.2 mi / 29.3 km)

Exploring the mountains and other natural features in Rutland

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

  • Pine Hill Park (0.8 mi / 1.3 km)
  • Pico Peak (7.5 mi / 12.1 km)
  • Killington Peak (8 mi / 12.9 km)
  • Lake Bomoseen (12 mi / 19.3 km)
  • Lake Hortonia (15.1 mi / 24.3 km)
  • Lake Saint Catherine (15.2 mi / 24.5 km)

Seasonal weather in Rutland

Rutland is well known for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, November or December, when snowfall averages 33 cm and temperatures average -4°C.

Transport options to and around Rutland

Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), the closest airport, located 5.7 mi (9.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Springfield, VT (VSF-Hartness State), which is 29.3 mi (47.1 km) away.

If you prefer train travel, the main station serving the city is Rutland Station.

Frequently asked questions

What is the best area to stay in Rutland when booking a holiday rental?
When considering a holiday rental in Rutland, Vermont, the Downtown area is an excellent choice. This vibrant neighbourhood offers a charming atmosphere with its historic buildings, local shops, and a variety of dining options. Staying here puts you in close proximity to attractions such as the Paramount Theatre, where you can enjoy live performances, and the Rutland Free Library, which is not only a beautiful structure but also a great spot for those interested in local history.

Another appealing area is the West Rutland neighbourhood, known for its scenic beauty and outdoor activities. This area provides access to the nearby West Rutland Marsh, a lovely spot for birdwatching and peaceful walks. It's a bit quieter than Downtown, making it great for those seeking relaxation while still being just a short drive from the town's amenities.

For those looking for a more rural experience, the East Mountain area is worth considering. This region boasts stunning views and is close to the Green Mountain National Forest, where you can enjoy hiking and other outdoor pursuits.
How much does it cost to rent a holiday home in Rutland?
Prices for holiday rentals in Rutland 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 Rutland 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 Rutland holiday house rentals?
You can find great discounts on house rentals in Rutland 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 Rutland ski resort rentals?
For those seeking ski resort rentals near Rutland, Vermont, the nearby Killington Ski Resort is a prime destination. Travellers can find a variety of rental options in the surrounding areas, particularly in Killington itself and the quaint village of Mendon. In Killington, many properties offer convenient access to the slopes, with amenities such as ski-in/ski-out capabilities, hot tubs for relaxing after a day on the mountain, and fully equipped kitchens for self-catering.

In Mendon, visitors can enjoy a more tranquil setting while remaining close to the ski action. Here, you'll find charming chalets and lodges that often feature rustic decor, spacious living areas, and fireplaces, providing a warm retreat for families and groups. Some rentals also include access to community amenities like indoor pools and fitness centres, ideal for unwinding after long days on the slopes.
What is the most popular type of holiday rental accomodation in Rutland?
In Rutland, holiday houses are the most popular type of rental, with approximately 43 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces superb for barbecues or enjoying the fresh Vermont air. Many of these homes are situated in residential neighbourhoods, providing a tranquil atmosphere for families or groups.

Apartments also have a popular presence, with around 21 options available, typically offering a more compact living space with essential amenities, ideal for couples or solo travellers. Additionally, there are about 17 condominiums that combine the comforts of home with resort-style amenities, often including pools or fitness centres.
Are there any family house rentals in Rutland?
In Rutland, Vermont, there are around 60 family-friendly holiday rentals available, making it an excellent choice for those travelling with children. The area offers a variety of homes, particularly in neighbourhoods like West Rutland and the historic downtown, where visitors can find spacious rooms equipped with essential amenities such as full kitchens, comfortable living areas, and outdoor spaces for children to enjoy.
Can I rent a holiday home with a pool or hot tub in Rutland?
In Rutland, Vermont, there are several holiday homes available for rent that feature pools and hot tubs, with around 16 options to choose from. This charming area offers a mix of amenities that cater to travellers looking for relaxation and recreation. Many of these properties are situated in scenic neighbourhoods, providing a beautiful backdrop for your stay.
Can I find long-stay holiday rentals in Rutland?
A long-stay holiday rental in Rutland 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 Rutland?
In Rutland, Vermont, there are several pet-friendly holiday house rentals available, with a total of 22 options to choose from. Visitors can expect a variety of amenities in these properties, such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy fresh air. Many rentals are conveniently located near local parks and recreational areas, making it easy for guests to take their pets for walks or outdoor adventures.
Are there any remote work holiday rentals in Rutland?
In Rutland, Vermont, there are numerous remote work holiday rentals available, with around 84 options to choose from. This charming town, set against the backdrop of the Green Mountains, offers a range of properties suited for those looking to blend work and leisure. Many rentals come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive environment.

Travellers can expect a variety of accommodations, from cosy apartments in the town centre to spacious homes with scenic views of the mountains. These properties often feature modern kitchens for self-catering, comfortable living areas for relaxation after work, and sometimes even outdoor spaces to enjoy the fresh Vermont air. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Rutland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Rutland 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 Rutland?
In Rutland, popular rental amenities typically include complimentary Wi-Fi, fully equipped kitchens featuring microwaves and essential cookware, as well as refrigerators to store food and beverages. These amenities enable guests to enjoy a comfortable and self-sufficient stay while exploring the area's attractions, such as the nearby Green Mountain National Forest and local ski resorts.
When is the best time to visit Rutland for a holiday rental?
The best time to visit Rutland for a holiday rental is during the peak summer months, particularly in July. This vibrant time of year draws many travellers eager to immerse themselves in the area's outdoor activities and stunning natural beauty. With temperatures typically hovering in the mid to high 20s Celsius, July provides ideal conditions for hiking, biking, and exploring the picturesque landscapes of the Green Mountains.

As you wander through Rutland, you'll have the chance to enjoy a variety of local festivals and events that celebrate the summer season. The bustling atmosphere is complemented by opportunities for delicious dining and shopping, making it a great getaway for those seeking both adventure and relaxation.

If you're looking for a more budget-friendly option, consider visiting in November. While this month is quieter, it offers a unique charm as the fall foliage transitions into a serene winter landscape. You can enjoy peaceful walks and the beauty of nature without the crowds, creating a truly intimate experience.
How early should I book a Rutland holiday rental?
Book your Rutland 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.
What are the top attractions in Rutland?
In Rutland, Vermont, visitors can engage in a variety of attractions that highlight the region's charm. The Rutland County Museum offers insights into the local history and culture, while nearby, the picturesque Pine Hill Park provides a network of trails superb for hiking and mountain biking.

The Paramount Theatre is a key cultural venue, hosting a range of performances from concerts to theatrical productions. For those interested in the great outdoors, the nearby Killington Resort is renowned for skiing in the winter and mountain biking in the summer, making Rutland an ideal base for both activities.
Can I change or cancel my Rutland home rental booking on Vrbo?
To find Rutland 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 Rutland 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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