Rutland holiday rentals

We found 2,174 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:6 Nov - 13 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$8,741
for 7 nights, 1 chalet
AU$1,249 per night
includes taxes & fees
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • Rutland Country Club (1.4 mi / 2.2 km)
  • 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)

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)
  • Beebe Pond (13.4 mi / 21.6 km)
  • Lake Hortonia (15.1 mi / 24.3 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 home?
One of the most in-demand neighbourhoods to get a Rutland holiday home is Mendon. When you book your holiday property, you'll enjoy having the whole place to yourself. So you won't have to share it with anyone apart from your people.
What is the most popular type of holiday home accommodation in Rutland?
According to our data, houses are the most sought-after type of property in Rutland. But having said that, everyone's idea of an epic stay is bound to be different. Stayz has holiday homes with every size, shape and budget in mind, and we'll help you to find your perfect match.
How much does it cost to rent a holiday home in Rutland?
Several things affect what you'll pay for your holiday home in Rutland, such as the length of stay, season and type of property. But, all of our holiday homes have one thing in common — incredible value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Rutland?
When you travel and the size and style of the property will influence the cost of your beachside escape. Click on your Rutland travel dates to see all your options on Stayz. Did someone just say "private pool"? Use the filters to pick the features and amenities you want.
Are there pet-friendly holiday homes in Rutland?
Pack a travel bag and a bone for your puppy dog because Rutland has 51 holiday homes that throw out the welcome mat to pets. Let your four-legged pal enjoy the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your dates and destination, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Rutland?
Grab your swimsuit and inflatable unicorn, because there are nine houses with a private pool in Rutland. Base yourself at one of these popular holiday homes and every day will be a pool day. Simply enter your travel dates into Stayz, then check the "pool" filter to find the perfect place to make a splash!
What are popular home amenities in Rutland?
When it comes to home amenities that guests are searching for in Rutland, a fireplace, nearby museums and ski-in/ski-out facilities are at the top of the list. With Stayz holiday homes, you'll find options to fit your style and taste, whether you're on a trip with family, friends or even pets.
Are there large group holiday homes in Rutland?
Rutland has 10 holiday homes that can accommodate 10 or more guests. These stays come with all the space you need to share good times with friends and family.
Are there holiday homes in Rutland that welcome kids?
With 51 family-friendly holiday homes to select from in Rutland, now is a great time to introduce your kids to the joys of travel. Click on our "Properties good for families" filter box to locate stays that feature conveniences perfect for holidaying families, like multiple bedrooms, pools, entertainment areas and bunk beds.
What are the top attractions for families in Rutland?
Keeping the kids amused during your Rutland holiday is child's play with these leading family-friendly attractions:

  • Killington Adventure Centre
  • McLaughlin Falls
  • Green Mountain Rock Climbing Centre

Are there one-bedroom holiday homes in Rutland?
Take your pick from 17 one-bedroom homes in Rutland. Whether you're searching for an apartment or a cabin, Stayz's one-bedroom properties are great if you don't need lots of room. One of the best things about having your own place? You'll never need to share your getaway with strangers.
Can I find two-bedroom holiday homes in Rutland?
Rutland has 14 two-bedroom holiday homes that you can choose from. Find a holiday home with all the comfort and space you're looking for at a price you'll love on Stayz.
Are there holiday homes with WiFi in Rutland?
You can choose from 30 holiday homes with WiFi in Rutland. If you want to disconnect from the world on your break, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Rutland?
Pick your dates and then make use of our filters to see holiday homes with ac in Rutland on Stayz. With 30 air-conditioned properties to choose from here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Rutland?
The minimum required age is normally 16, 18 or 21. It can vary between properties on Stayz, so check the rules of your chosen Rutland holiday home before making a booking.
How long can I rent a holiday home in Rutland for?
The amount of time you can book a Rutland holiday home for is up to each property. Simply enter your preferred travel dates to browse available options that offer long-term stays. They have everything you need to make your extended getaway more comfortable and enjoyable, such as kitchens and air conditioning. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can hang around longer for less.