Rutland holiday homes

We found 2,216 holiday rentals — enter your dates for availability
Select from 56 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:25 Dec - 1 Jan

Property grounds
Living area
Pool
Living area
Exceptional
(16 reviews)

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish

8% off
NZ$35,681
for 7 nights, 1 cabin
NZ$5,097 per night
includes taxes & fees
Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
The first floors open plan is great for large groups.
Fully stocked kitchen with plenty of room to prepare a family dinner
Deer Room - 1st floor bedroom with a queen bed.
Bear Room - 2nd Floor bedroom with a king bed, tv with roku and sitting area.
Exceptional
(11 reviews)

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester

8% off
NZ$7,977
for 7 nights, 1 chalet
NZ$1,140 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Adults upstairs & kids in Gameroom hangout TV, DVD, VCR & large movie library
Morning coffee on the front deck overlooking our wooded lot?
Beautiful 4-season ski chalet on Okemo less than a mile to ski base
Dining
Exceptional
(133 reviews)

Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

Ludlow

8% off
NZ$13,301
for 7 nights, 1 chalet
NZ$1,900 per night
includes taxes & fees
Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12
Dining
Terrace/patio
Family room with gas fireplace, Frame TV, Sonos over Vermont barn mantle.
Exterior
Exceptional
(97 reviews)

5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, Summer Pool

Killington

8% off
NZ$26,642
for 7 nights, 1 home
NZ$3,806 per night
includes taxes & fees
5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, Summer Pool
Room
Living area
Outdoor dining
Dining
Exceptional
(5 reviews)

Updated Home, Near Killington and Okemo, Hot Tub, EV Charger

Rutland

8% off
NZ$26,375
for 7 nights, 1 home
NZ$3,768 per night
includes taxes & fees
Updated Home, Near Killington and Okemo, Hot Tub, EV Charger
Kitchen Bar
Image from trailhead
Living Room - looking out over mountains
Lower Level Bar/Kitchenette
Exceptional
(67 reviews)

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington

8% off
NZ$30,345
for 7 nights, 1 home
NZ$4,335 per night
includes taxes & fees
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Interior
Pool
Outdoor dining
Property grounds
Exceptional
(35 reviews)

Reading Farms Estate

Reading

8% off
NZ$56,877
for 7 nights, 1 home
NZ$8,125 per night
includes taxes & fees
Reading Farms Estate
The Great Room
Front of home (late fall sunset)
The Great Room and dining table - seats 10
Covered outdoor patio with views of the lake, connecting to king bedroom
Exceptional
(20 reviews)

5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C

Ludlow

8% off
NZ$22,212
for 7 nights, 1 home
NZ$3,173 per night
includes taxes & fees
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
Winter looking Southeast
Master bedroom looking Southwest (upper level
Den area main level (baby not included!)
Kitchen (main level)
Exceptional
(25 reviews)

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

Mount Holly

8% off
NZ$9,914
for 7 nights, 1 cabin
NZ$1,416 per night
includes taxes & fees
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!
Outdoor dining
Dining
Exterior
Private kitchen
Exceptional
(29 reviews)

North Porch Farmhouse

Rochester

8% off
NZ$4,048
for 7 nights, 1 home
NZ$578 per night
includes taxes & fees
North Porch Farmhouse
Living area
Exterior
Interior
Dining
Exceptional
(13 reviews)

Charming getaway cottage by the Green Mountains/Killington/Okemo in Vermont!

Wallingford

6% off
NZ$5,658
for 7 nights, 1 home
NZ$808 per night
includes taxes & fees
Charming getaway cottage by the Green Mountains/Killington/Okemo in Vermont!
Dining
Pool in the nearby recreational building
Room
Living area
Exceptional
(140 reviews)

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

Ludlow

8% off
NZ$29,138
for 7 nights, 1 apartment
NZ$4,163 per night
includes taxes & fees
Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace
Exterior
Outdoor dining
Interior
Dining
Exceptional
(125 reviews)

Waterfront Ponds, Beautiful , 51 Acre Property Retreat

Brandon

7% off
NZ$3,610
for 7 nights, 1 home
NZ$516 per night
includes taxes & fees
Waterfront Ponds, Beautiful , 51 Acre Property Retreat
Bedroom #2 Queen bed with large windows & french doors
Front of house, early spring
Private driveway with ramp to enter house. Gently babbling stream in the front
Open living room with french doors, huge windows & vaulted ceiling
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
NZ$7,511
for 7 nights, 1 home
NZ$1,073 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Living area
Cozy Cabin Luxury!
Interior
Living area
Exceptional
(7 reviews)

Rare Private Log VT Lodge Cabin Stunning Mountain & Stream Views near Killington

Proctor

8% off
NZ$7,248
for 7 nights, 1 cabin
NZ$1,035 per night
includes taxes & fees
Rare Private Log VT Lodge Cabin Stunning Mountain & Stream Views near Killington
Exterior
Living area
Property grounds
Interior
Exceptional
(6 reviews)

Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort

Chittenden

8% off
NZ$10,620
for 7 nights, 1 home
NZ$1,517 per night
includes taxes & fees
Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort
Bedroom #2
Main deck
Exterior
Dinning Area
Exceptional
(30 reviews)

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

Ludlow

8% off
NZ$8,867
for 7 nights, 1 home
NZ$1,267 per night
includes taxes & fees
Lake Front home on Lake Rescue. Sunset views, peaceful home with a private dock.
Living room with cathedral ceiling, wood-burning fireplace, and 50" TV
Living area
Private kitchen
Mud-room, with firewood and kindling provided
Exceptional
(14 reviews)

Spacious Townhouse on the Killington Access Road

Killington

10% off
NZ$15,233
for 7 nights, 1 home
NZ$2,176 per night
includes taxes & fees
Spacious Townhouse on the Killington Access Road
Room
Interior
Exterior
Private kitchen
Exceptional
(11 reviews)

Main St Studio - Newly Updated!

Ludlow

8% off
NZ$4,729
for 7 nights, 1 apartment
NZ$676 per night
includes taxes & fees
Main St Studio - Newly Updated!
Sunrise view from our deck
Exterior
Eat in kitchen
Mud room with Ski Closet
Exceptional
(34 reviews)

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

Ludlow

8% off
NZ$18,628
for 7 nights, 1 apartment
NZ$2,661 per night
includes taxes & fees
OKEMO Trailside Ski Condo, Walk to Sachem Trail, Sleeps 8
Interior
Exterior
Dining area seats 8
Full kitchen
Wonderful
(5 reviews)

2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area

Cavendish

16% off
NZ$3,228
for 7 nights, 1 apartment
NZ$461 per night
includes taxes & fees
2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area
Interior
Outdoor dining
Private kitchen
Interior
Exceptional
(83 reviews)

As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.

Ludlow

8% off
NZ$10,478
for 7 nights, 1 home
NZ$1,497 per night
includes taxes & fees
As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.
Cottage front
Deck with chiminea
Living room, antique wardrobe with TV and stereo
Living/Dining room with gas stove
Exceptional
(86 reviews)

Cozy Historic Hilltop Cottage with Mount Ascutney View

Windsor

8% off
NZ$2,721
for 7 nights, 1 cottage
NZ$389 per night
includes taxes & fees
Cozy Historic Hilltop Cottage with Mount Ascutney View

  • Peace of mind

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  • 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 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)
  • 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 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Rutland holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Rutland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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