Rutland holiday rentals

We found 2,164 holiday rentals — enter your dates for availability
Select from 48 houses, 18 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:20 Nov - 27 Nov

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

Property grounds
10 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)

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

Ludlow

8% off
Price is AU$8,636
for 7 nights, 1 chalet
AU$1,234 per night
includes taxes & fees
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

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Why visit Rutland

  • Charming downtown: Explore Rutland's vibrant downtown, filled with unique shops and a rich local culture.
  • Outdoor activities: Enjoy a range of outdoor adventures, including skiing and sports, set against stunning natural backdrops.
  • Scenic parks and lakes: Discover beautiful parks and serene lakes perfect for relaxation and family-friendly outings.
  • Historic attractions: Visit local museums and heritage sites that showcase Rutland's fascinating history.
  • Welcoming atmosphere: Experience the friendly locals and community spirit that make Rutland an inviting holiday destination.

Popular types of accommodation in Rutland

Discover Rutland, Vermont, a charming city offering a blend of history and modernity. Enjoy attractions like scenic parks, local museums, and heritage sites. Rutland accommodation includes private holiday homes, cosy condos, and inviting cabins, ensuring the best Rutland accommodation for every traveller. Check our room rates for competitive stays in Rutland, VT homes designed for comfort and exploration.

  • Private Holiday Homes: Enjoy the utmost privacy and space in a charming holiday retreat, the top choice for visitors in Rutland.
  • Condos: Experience modern comforts in cosy, well-equipped condominiums, a popular selection among holidaymakers.
  • Cabins: Delight in the rustic appeal of a secluded cabin, ideal for a peaceful getaway.
  • Cottages: Revel in the quaint charm of a traditional cottage, perfect for a relaxed stay.
  • Apartments: Benefit from the convenience and flexibility of a well-appointed apartment during your visit.**

Top attractions near Rutland

Rutland, Vermont, offers a delightful blend of outdoor adventure and family-friendly activities. Visitors can explore beautiful parks and lakes, making it ideal for skiing and sports holidays. Strolling through downtown Rutland reveals charming shops and local culture, while nearby natural attractions provide stunning scenery. Whether you're seeking an active getaway or a peaceful retreat, Rutland promises memorable experiences for every traveller.

  • Lake Bomoseen: A picturesque lake renowned for its stunning scenery, ideal for romantic getaways and outdoor activities. Enjoy leisurely days by the beach, surrounded by nature.
  • Wilson Castle: A fascinating historic site just a short distance from Rutland, Wilson Castle showcases remarkable architecture and rich cultural heritage, providing a glimpse into Vermont's past.
  • Dorset Quarry: A scenic natural feature perfect for budget-friendly adventures, where you can meet friendly locals and explore the unique landscape of this historic quarry.

Things to do recommended for couples

Discover Rutland, Vermont, a charming retreat for couples. Enjoy cosy walks and intimate dining in local hidden gems, blending rustic charm with modern comforts for an unforgettable escape.

Things to do recommended for families

Families can explore the delightful Hood Museum and take gentle walks along scenic trails. Enjoy a visit to the charming local market and sample a variety of home-baked treats in a quintessential New England town.

Things to do recommended for groups

Discover the charm of Rutland, Vermont, where you can embark on scenic hikes and cycle along picturesque trails, whilst immersing yourself in local culture with cosy pub visits and lively group events.

*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 Rutland

When travelling with a group, family, pets, or seeking longer stays, it’s essential to filter according to your key priorities. Here are some helpful Stayz booking tips to assist you.

  • Traveling to Rutland with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Stayz.
  • Traveling to Rutland with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Rutland: For some, a family holiday is not complete without their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Rutland: If you're searching for holiday rentals with special offers 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 consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Rutland

Rutland, Vermont, is a charming city that offers a delightful blend of adventure and relaxation. Visitors can explore its vibrant downtown, rich in history and local culture, while enjoying the scenic beauty of Rutland County. Ideal for skiing and outdoor sports, Rutland also boasts family-friendly activities and a welcoming atmosphere. Whether you're seeking recreation, romantic strolls, or simply the company of friendly locals, Rutland is a perfect destination for a memorable holiday experience.

  • Killington: Located 18km from Rutland, Killington offers a delightful blend of adventure and scenic beauty. Renowned for its skiing heritage, the city attracts travellers seeking winter sports and outdoor excitement. Its ski fields and renowned resort provide opportunities for skiing and snowboarding amidst a backdrop of majestic mountains and a serene lake. Beyond the slopes, visitors can explore nearby national and state parks, immersing themselves in the natural splendour of the area.
  • Chittenden: Just 14km from Rutland, Chittenden is celebrated for its vibrant outdoor experiences. The city is a haven for skiing enthusiasts, with its well-maintained ski fields and resort facilities offering ample opportunities for both novice and experienced skiers. The local landscape, featuring a picturesque lake, national state park, and rugged mountains, provides a perfect setting for adventure and relaxation amid nature's beauty.
  • Castleton: Situated 16km from Rutland, Castleton is a charming destination known for its romantic and scenic allure. Ideal for those seeking an outdoor escape, the city offers access to popular ski fields and resorts for winter sports. The nearby lake, alongside a modern college university and a national state park, enriches the cultural and natural experience, making Castleton a delightful blend of scenic tranquillity and dynamic outdoor pursuits.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 Stayz is simple

Looking to reduce costs on your next holiday? Consider flexible travel dates, as prices may vary. Moreover, extending your stay can often result in significant savings. To locate the ideal Stayz property that meets your budget, utilise our filters to search by price, location and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board offers a user-friendly area to plan new journeys, continue from where you last paused, or view and arrange your travel plans. You can easily find the properties you’ve saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/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 National Golf Course (9.8 mi / 15.8 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 is not only the heart of the city but also offers a charming atmosphere with a variety of dining and shopping options. You can explore the local arts scene at the Paramount Theatre, which frequently hosts performances and events, making it a cultural hub in the area. Additionally, the nearby Rutland County Museum provides insight into the region's rich history, showcasing intriguing exhibits that appeal to both locals and visitors alike.

Another appealing option is the West Rutland area, known for its scenic views and proximity to outdoor activities. If you enjoy nature, the nearby Pine Hill Park boasts extensive trails superb for hiking and biking, allowing you to immerse yourself in the stunning Vermont landscape. This area provides a more relaxed vibe while still being conveniently close to the amenities of the city centre.
Where are the best Rutland ski resort rentals?
For the best ski resort rentals near Rutland, Vermont, travellers should consider the proximity to the Killington and Pico Mountain areas, which are both within a short drive. The town of Killington, known for its vibrant ski culture, offers a variety of rental options, including spacious chalets and comfortable condos. Many of these properties come equipped with modern amenities such as fully stocked kitchens, hot tubs, and cosy fireplaces, superb for unwinding after a day on the slopes.

In Rutland itself, visitors can find charming townhouses and rustic cabins that provide easy access to both the ski resorts and local attractions. These rentals often feature amenities like Wi-Fi, laundry facilities, and outdoor spaces for enjoying the scenic Vermont landscape. Additionally, Rutland boasts a lively downtown area with restaurants, shops, and cultural attractions, making it a convenient base for both skiing and exploring.

For those looking for a more secluded experience, the nearby Green Mountain National Forest offers a range of properties located in nature, where guests can enjoy peace and quiet along with outdoor activities like snowshoeing and cross-country skiing.
What is the most popular type of holiday rental accomodation in Rutland?
In Rutland, holiday houses are the most prevalent type of holiday rental, with approximately 176 available throughout the area. These spacious properties are typically found in family-friendly neighbourhoods, offering multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing after a day of exploration. Many also come with amenities like barbecue facilities and game rooms, making them great for larger groups or families.

Additionally, there are around 60 condos and 60 apartments, which provide a more compact living option with convenient amenities, often including pools and fitness centres, ideal for those looking for a more social atmosphere. For a quaint experience, about 24 cabins and 12 cottages are also available, set in picturesque surroundings, great for travellers seeking a rustic retreat.
Are there any family house rentals in Rutland?
In Rutland, Vermont, family-friendly house rentals are plentiful, with around 51 options available. This charming city offers a variety of accommodations suitable for families, often located in neighbourhoods close to local attractions. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces great for children to play. Amenities such as Wi-Fi and laundry facilities are commonly included, ensuring a comfortable and convenient stay.

Visitors can explore the nearby Green Mountain National Forest for hiking and outdoor activities, while the vibrant downtown area of Rutland boasts shops, restaurants, and cultural sites.
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 17 options to choose from. This charming town offers a mix of amenities that cater to visitors seeking relaxation and outdoor activities. Many of these properties come equipped with private pools and hot tubs, great for unwinding after a day of exploring the beautiful Green Mountains.

Travellers can expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces for barbecuing or enjoying the scenic views. Some rentals might also feature fireplaces and game rooms, adding to the comfort and entertainment options for families or groups.
Are there pet-friendly house rentals in Rutland?
In Rutland, Vermont, there are numerous pet-friendly house rentals available, offering travellers a welcoming environment for their furry companions. Many of these properties come equipped with essential amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas, making them ideal for families or groups.

The area is known for its access to outdoor activities, with nearby parks and natural attractions great for pet owners. The nearby Green Mountain National Forest offers expansive trails suitable for hiking with pets, while local parks provide open spaces for leisurely walks. Additionally, Rutland has pet-friendly cafes and shops where visitors can enjoy the local scene with their pets.
Are there any remote work holiday rentals in Rutland?
In Rutland, Vermont, there are numerous remote work-friendly holiday rentals available, with around 312 options to choose from. Many of these properties cater to the needs of remote workers, offering amenities such as dedicated workspaces complete with desks and chairs, as well as free Wi-Fi to ensure a reliable internet connection. Some rentals may even provide additional features like printers for added convenience.

The town itself is rich in charm, with easy access to local eateries and shops, making it a pleasant environment for both work and leisure. Additionally, Rutland is near outdoor attractions, allowing for refreshing breaks amidst nature, whether you're interested in hiking or simply enjoying the scenic surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Rutland?
In Rutland, popular rental amenities include fully equipped kitchens, superb for preparing meals after a day of exploring. Many accommodations feature cosy fireplaces, adding a warm atmosphere, especially during the colder months. Additionally, travellers can expect coffee and tea makers for their morning brews, along with convenient onsite parking. For those looking to enjoy winter sports, several rentals also highlight nearby skiing locations, making it easy to hit the slopes.
When is the best time to visit Rutland for a holiday rental?
The best time to book a holiday rental in Rutland is during the peak season, which runs from July to September. This vibrant period attracts visitors keen to immerse themselves in the beauty of Vermont's summer landscape, with warm temperatures averaging between 15 to 27 degrees Celsius. Activities abound, from hiking in the Green Mountains to exploring the nearby lakes, making it an ideal time for outdoor adventures and leisurely sightseeing.

July stands out as the most popular month, offering a lively option with plenty of local events and festivals. Visitors can enjoy outdoor concerts, farmers' markets, and the enchanting scenery that Rutland has to offer. The comfortable weather makes it great for exploring charming downtown shops and enjoying the picturesque parks that dot the area.

For those looking to save a bit on their holiday rental, November is a wonderful alternative. While it falls outside the high tourist season, it showcases the tranquil beauty of late autumn, with stunning fall foliage lingering into early November. This quieter month allows for serene walks and a chance to appreciate the natural surroundings without the hustle and bustle of peak season.
What are the top attractions in Rutland?
In Rutland, Vermont, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The Rutland County Courthouse, with its stunning architecture, is a top landmark that captures the town's historical charm. Nearby, the Paramount Theatre offers a vibrant schedule of live performances, making it a cultural hub for residents and visitors alike.

For those who appreciate the outdoors, the nearby Pine Hill Park provides extensive hiking and biking trails, great for exploring the picturesque landscape. The area is also known for its proximity to the Green Mountains, where outdoor enthusiasts can partake in skiing, snowboarding, and other winter sports during the colder months.

Additionally, the local farmers' market is a delightful spot to experience Vermont's fresh produce and artisanal products, typically held in the warmer months and showcasing the region's agricultural heritage.
Are all fees included in the Rutland 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 Rutland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Rutland holiday homes?
You can find great discounts on holiday homes in Rutland 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 Rutland holiday home booking on Stayz?
To find Rutland 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 Rutland?
A long-stay holiday home 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 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 Rutland holiday home?
Book your Rutland 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 Rutland?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Rutland 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.