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Rutland, VT vacation rentals
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Best Vacation rentals and Airbnb offers in Rutland, VT

Our Favorite Family-Friendly Vacation Rentals in Rutland, VT

Booking a family-oriented vacation rental in Rutland, VT keeps you close to top city attractions for a stress-free getaway.

Spacious Ski Lodge In Killington With Game Room And Wood Burning Fireplace. - Rutland, VT
9.4 10 reviews
Rutland, VT
07/03 – 07/05
$676/nighttotal: $1352 (2 )

Spacious Ski Lodge In Killington With Game Room And Wood Burning Fireplace.

4 9
apartment , Killington
This chalet is located in a peaceful wooded area of Killington, just minutes away from the Killington Ski Area and golf courses. It has received excellent user ratings, making it a popular choice for travelers. This four-bedroom, three-bathroom home comfortably sleeps 10 guests, offering ample space for families or groups of friends. The chalet boasts a game room, multiple living areas, a fully equipped kitchen, and outdoor space with a gas grill, ensuring a memorable stay for everyone.
Spacious Vermont Getaway 7 Br/4.5 Ba - Close To Skiing - Biking - Golf - Hiking - Rutland, VT
9.4 137 reviews
Rutland, VT
07/03 – 07/05
$1775/nighttotal: $3550 (2 )

Spacious Vermont Getaway 7 Br/4.5 Ba - Close To Skiing - Biking - Golf - Hiking

7 15
apartment , Killington
This 10-bedroom vacation home is located in the mountains of Killington, Vermont, close to the Killington Resort and the Calvin Coolidge Historic Site. This property has earned excellent user ratings, making it a popular choice for travelers seeking a comfortable and enjoyable stay.
This expansive 5,010 square foot home comfortably accommodates up to 16 guests with 7 bedrooms and 6 bathrooms. Amenities include a fully equipped kitchen, multiple fireplaces, a swimming pool, a Jacuzzi, a sauna, a spa, a terrace, a garden, and parking.
Spacious Modern Mountain Retreat W/ Fireplace - Rutland, VT
Rutland, VT
07/03 – 07/05
$1198/nighttotal: $2396 (2 )

Spacious Modern Mountain Retreat W/ Fireplace

5 9
apartment , West Rutland
This private, single-family home in West Rutland sits on two scenic acres, offering a secluded setting just 20 to 30 miles from Pico, Killington, and Okemo ski resorts, and 15 miles from Lake Bomoseen Lodge.
This 2360 square foot residence accommodates up to 10 guests with 5 bedrooms and 3 bathrooms, featuring an open-concept great room with a full kitchen and wet bar, two living areas, a mudroom for gear, and an outdoor patio with a grill and fire pit, plus an on-site playground.
Authentic Log Home With Pico Views And Hot Tub - Rutland, VT
9.4 60 reviews
Rutland, VT
07/03 – 07/05
$833/nighttotal: $1666 (2 )

Authentic Log Home With Pico Views And Hot Tub

5 9
apartment , Killington
This Killington condo is located directly across from the Pico Mountain entrance, offering mountain views and convenient access, just a 10-minute drive to Killington's K1 base lodge and an 8-minute drive to Ramshead lodge.
This family-friendly apartment boasts 420 square feet, accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, and features a full kitchen, air conditioning, a swimming pool, hot tub, and is situated near Gifford Woods State Park.

Best Rutland, VT vacation rentals with parking

Vermont Shear Heaven Retreat - Rutland, VT
9.7 21 reviews
Rutland, VT
07/03 – 07/05
$1655/nighttotal: $3310 (2 )

Vermont Shear Heaven Retreat

4 9
apartment , Rutland
This Rutland vacation rental is conveniently located on Route 7, just a short drive from Killington and Pico ski resorts. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience. This spacious home comfortably accommodates up to 10 guests with 4 bedrooms and 3 bathrooms. It offers a fully equipped kitchen, a wood-burning fireplace, a private garden, and parking for multiple vehicles. Guests can enjoy nearby activities like skiing, hiking, and biking, or simply relax and enjoy the peaceful surroundings.
The Killington Chalet 2-hot Tubs, Sauna, 24 Pair Boot And Glove Dryer - Rutland, VT
Rutland, VT
07/02 – 07/04
$1849/nighttotal: $3698 (2 )

The Killington Chalet 2-hot Tubs, Sauna, 24 Pair Boot And Glove Dryer

8 15
chalet , Killington
This Killington vacation home is located 4.5 miles from Killington Peak, 1.2 miles from Gifford Woods State Park, and 16 miles from Rutland State Airport.
This 4000-square-foot chalet boasts two hot tubs, a sauna, a 24-pair boot and glove dryer, free Wi-Fi, and private parking, plus fully equipped kitchens in some rooms.
Rutland's Hidden Gem: Renovated 2 Br/1ba In Town - Rutland, VT
9.5 60 reviews
Rutland, VT
09/17 – 09/21
$520/nighttotal: $2080 (4 )

Rutland's Hidden Gem: Renovated 2 Br/1ba In Town

2 2
apartment , Rutland
This Rutland, Vermont home is conveniently located 0.7 miles from Rutland Regional Medical Center and 1.9 miles from downtown Rutland, offering easy access to area attractions.
This two-bedroom rental sleeps six, features a fully equipped kitchen with stainless steel appliances, a modern open floor plan, and amenities including a smart TV, Wi-Fi, and EV charging (fee applies).
Sunset Notch- Hot Tub, Cold Plunge, Hiking, Views! - Rutland, VT
Rutland, VT
09/17 – 09/21
$756/nighttotal: $3024 (4 )

Sunset Notch- Hot Tub, Cold Plunge, Hiking, Views!

4 2
apartment , Mendon
This mountain retreat, set on over 10 acres in Rutland, offers breathtaking sunset and mountain views, a serene forest environment, and convenient access to Killington and Pico resorts, hiking trails, and Rutland's dining scene, including Wilson Castle and the Calvin Coolidge Historic Site.
This 4-bedroom, 3-bathroom condo sleeps up to 8 guests and features a fully equipped kitchen, a family room with a wet bar and fireplace, a private hot tub, a terrace, a garden, and parking, with discounted lift tickets available for guests.

Frequently Asked Questions about vacation rentals in Rutland, VT

  • Which walking or cycling routes are the best in Rutland, VT?

    The Rutland Recreation Path is a great option for walking or biking. It follows the route of the old railroad line and goes right through the heart of the city. For a longer ride, you can head out to the Killington Bike Path, which runs for 10 miles along the scenic Killington River.
  • What are the best Airbnb and vacation rentals in Rutland, VT?

    Your Home Away From Home, The Look Out and Home Sweet Grove Street are the most popular Airbnb and vacation rentals in Rutland, VT among travelers.

  • What sports or outdoor activites can visitors enjoy in and around Rutland, VT?

    Rutland is a great place to enjoy all kinds of outdoor activities. You can go skiing or snowboarding at Killington or Pico in the winter. In the summer, you can go hiking, biking, fishing, or kayaking. There are also a lot of golf courses in the area.
  • What are the most popular Airbnbs in Rutland, VT?

    Among the Airbnbs in Rutland, VT, Your Home Away From Home, The Look Out and The House Of Views are the most popular ones.

  • What other towns or cities can be easily accessed from Rutland, VT?

    Rutland is a great base for exploring the surrounding area. You can easily get to Burlington, Vermont, which is about an hour away. You can also drive to Montpelier, the state capital, in about 45 minutes. And if you want to head to the mountains, Killington and Stowe are both within a two-hour drive.
  • What are the best vacation rentals with a pool in Rutland, VT?

  • What amenities are commonly available in vacation rentals in Rutland, VT?

    Most vacation rentals in Rutland come with basic amenities like a kitchen, bathroom, and laundry facilities. Many also have extra features like a fireplace, hot tub, or private deck. Some rentals are even located on the lake.
  • What are the best rentals for families and kids in Rutland, VT?

    The best rentals for families and kids in Rutland, VT are Your Home Away From Home, The Look Out and The House Of Views.

  • What time of year is best to rent a vacation rental Rutland, VT?

    The best time to visit Rutland depends on what you're looking for. If you want to enjoy the fall foliage, come in October. If you're into winter sports, January and February are great months. And if you want to enjoy the warm weather, July and August are perfect.
  • What are the best rentals or Airbnbs with a jacuzzi in Rutland, VT?

  • What are the local dishes in Rutland, VT region?

    You've got to try a Vermont cheddar cheese, it's a classic. And you can't go wrong with a maple syrup-based treat. We're known for our maple creemees and maple-glazed donuts. And of course, you can't forget the local craft beers. We have a lot of great breweries in the area.

Destinations nearby

Find the Best Vacation Rentals with Balconies in Rutland, VT

Enjoy stunning views from your private terrace when you book one of these vacation rentals in Rutland, VT.

Winter Lore  4br Mountain Getaway W/ Hot Tub, Game Room & Pet-friendly Vibes! - Rutland, VT
9.6 51 reviews
Rutland, VT
09/17 – 09/21
$633/nighttotal: $2532 (4 )

Winter Lore 4br Mountain Getaway W/ Hot Tub, Game Room & Pet-friendly Vibes!

4 2
apartment , Mendon
This Mendon vacation home is surrounded by mountains, providing picturesque views. It is within 6 miles of Green Mountain Rock Climbing Center, Rutland Regional Medical Center, and Paramount Theater. It has excellent user and location ratings and is very clean.
The house has 4 bedrooms and can accommodate up to 10 guests. It has a fully equipped kitchen, a spacious layout, and is smoke-free. Guests can enjoy amenities such as a swimming pool, Jacuzzi, terrace, garden, spa, and fitness center. It also has an arcade/game room, a spa tub, a fireplace, and a balcony.
Large Ski Ranch Hot Tub Close To Killington Pets Ok - Rutland, VT
9.6 4 reviews
Rutland, VT
09/17 – 09/21
$982/nighttotal: $3928 (4 )

Large Ski Ranch Hot Tub Close To Killington Pets Ok

4 2
apartment , Mendon
This Mendon estate offers four bedrooms and two bathrooms, accommodating up to eight guests with amenities including internet and air conditioning.
Located just 1 mile from Pico Mountain at Killington Ski Resort and Killington Resort, this property provides easy access to outdoor activities and is also close to the Green Mountain Rock Climbing Center and Vermont State Fairgrounds.
Bear8 Sleeps 20, Ac, Pool, Close To Resort, Fireplaces - Rutland, VT
Rutland, VT
07/03 – 07/05
$3834/nighttotal: $7668 (2 )

Bear8 Sleeps 20, Ac, Pool, Close To Resort, Fireplaces

8 15
apartment , Killington
This spacious Killington condo boasts ski-in/ski-out access, proximity to Killington Resort and Killington Golf Course (under 1 mile), and is within a 15-minute drive of the Killington Adventure Center and Black Dog Sports.
This 2,710-square-foot residence features eight bedrooms, four bathrooms, accommodates sixteen guests, and includes a fully equipped kitchen, private balcony, garden, and free WiFi.
Merry Maple Getaway - Rutland, VT
9.8 98 reviews
Rutland, VT
07/02 – 07/04
$703/nighttotal: $1406 (2 )

Merry Maple Getaway

5 15
apartment , Mendon
This family-friendly vacation home is located in Rutland, just a short 15-minute walk from Pico Mountain at Killington Ski Resort and Golden Express Quad, making it a great choice for skiers and families. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This 5-bedroom, 2-bathroom home can accommodate up to 15 guests. The property includes a fully equipped kitchen, a fireplace, a terrace, a garden, and parking, along with a riverfront location and proximity to other attractions like Deer Leap Trail and Fire Tower.

Top Dog-Friendly Vacation Rentals in Rutland, VT

Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Rutland, VT are steps away from dog parks and city walks.

Quaint City Cottage Just Minutes From Killington - Rutland, VT
9.4 25 reviews
Rutland, VT
09/17 – 09/21
$481/nighttotal: $1924 (4 )

Quaint City Cottage Just Minutes From Killington

3 2
apartment , Rutland
This Rutland vacation home is located in a quiet neighborhood, approximately 15 minutes from Killington and Pico ski resorts and close to local restaurants and nightlife.
The three-bedroom, two-bathroom house sleeps six guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and Wi-Fi.
Cabin ∙ 2 Bedrooms ∙ 4 Guests - Rutland, VT
Rutland, VT
09/17 – 09/21
$289/nighttotal: $1156 (4 )

Cabin ∙ 2 Bedrooms ∙ 4 Guests

2 2
cabin , Chittenden
This Chittenden cottage is located on a private road with pond views, 0.5 miles from Chittenden Reservoir and near Killington and Pico ski resorts.
This rental sleeps four guests and features two bedrooms, one bathroom, a full kitchen, air conditioning, a sundeck, and a fire pit, with a Roku TV and WiFi available.
Muwu In Killington Area - Rutland, VT
9.5 52 reviews
Rutland, VT
09/17 – 09/21
$451/nighttotal: $1804 (4 )

Muwu In Killington Area

1 2
apartment , Rutland
This Rutland, Vermont vacation home boasts a prime location, a 15-minute drive from Killington Ski Resort and 2 minutes from the Rutland Country Club, with direct access to a hiking trail.
Sleeping up to 10 guests comfortably, this three-bedroom, two-bathroom house features a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a Jacuzzi, a garden, parking, and high-end furniture including 12-inch memory foam mattresses; a $120 pet fee applies (max 2 pets).
Bigelow Chalet At Killington: 8br/4.5 Ba Pet Friendly Home W/ Hot Tub, Fireplace. - Rutland, VT
8.8 3 reviews
Rutland, VT
07/03 – 07/05
$2053/nighttotal: $4106 (2 )

Bigelow Chalet At Killington: 8br/4.5 Ba Pet Friendly Home W/ Hot Tub, Fireplace.

8 15
chalet , Killington
This family-friendly cabin is located just a short drive from Killington Resort and Gifford Woods State Park, offering easy access to the area's best outdoor activities. The surrounding area also provides opportunities for exploring nature, wildlife viewing, and historical sites.
This 8-bedroom, 5-bathroom vacation rental can comfortably accommodate up to 16 guests. The chalet features a fully equipped kitchen, a hot tub, a fireplace, a game room, and a spacious outdoor area with a barbecue grill.
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