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

Browse Vacation Rentals in the Historic District of Rutland, VT

From vibrant downtown areas to historic streets, these Rutland, VT vacation rentals put you close to everything worth seeing.

Home Away From Home - Rutland, VT
9.5 53 reviews

Home Away From Home

apartment, Rutland
This spacious Rutland, Vermont apartment rental is located two blocks from downtown Rutland, offering easy access to local amenities and a 20-minute drive to both Killington and Okemo ski resorts.
The 2000-square-foot, three-bedroom unit sleeps up to 10 guests and features ample parking, on-site laundry, and proximity to Pine Hill Park and Killington Adventure Park mountain biking trails.
Rustic Vermont Cottage For Families - Self Checkin - Rutland, VT
9.6 113 reviews

Rustic Vermont Cottage For Families - Self Checkin

apartment, Rutland
This 3-bedroom house is located in a residential area of Rutland, just a 20-minute drive from Killington and a 15-minute drive from Pico. Guests consistently rate the property excellent for cleanliness, location, and overall experience.
The home can comfortably accommodate up to 12 guests and features a well-equipped kitchen with modern appliances, a comfortable living space with a flat-screen TV, and a spacious garden. Enjoy convenient amenities like self check-in, fast Wi-Fi, and a dedicated parking space.
The Green Mountain Nook - Rutland, VT
10 8 reviews

The Green Mountain Nook

apartment, Rutland
This private attached studio apartment in Rutland offers a tranquil Vermont retreat on the outskirts of the city, providing proximity to the Green Mountains for outdoor exploration.
This studio accommodates two guests and features a well-equipped kitchenette with a fridge, freezer, and microwave, along with air conditioning, parking, and internet access for a comfortable stay.
Spacious Central 4br, Ski, Bike,hike, Explore Downtown - Rutland, VT
10 5 reviews

Spacious Central 4br, Ski, Bike,hike, Explore Downtown

apartment, Rutland
This Rutland apartment rental is conveniently located downtown, an 8-minute walk from the Paramount Theatre and a 7-minute walk from the Chaffee Art Center, near Lake Champlain.
This four-bedroom, three-bathroom unit sleeps twelve guests and boasts a fully equipped kitchen, in-unit laundry, a terrace, and on-site parking, plus access to a spa and garden.

Best Rutland, VT vacation rentals with air conditioning

Spacious Ski Chalet With Pool Table & Mountain Views - Rutland, VT
10 1 review

Spacious Ski Chalet With Pool Table & Mountain Views

apartment, Rutland
This Rutland vacation home is conveniently located within one mile of the Paramount Theater and Green Mountain Rock Climbing Center, and within two miles of Rutland Regional Medical Center and the Vermont State Fairgrounds, offering easy access to Rutland Station.
This four-bedroom, three-bathroom house sleeps ten guests and includes amenities such as a washer, dryer, and hair dryer, providing a self-catering option with laundry facilities ideal for longer stays.
3000 Sq Feet With Stocked Kitchen And Huge Mudroom - Rutland, VT
10 76 reviews

3000 Sq Feet With Stocked Kitchen And Huge Mudroom

apartment, Rutland
This 3-bedroom apartment is situated in a quiet neighborhood near Rutland, Vermont, just 8 minutes from Pico Mountain and less than 15 minutes from Killington Mountain. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is perfect for families or groups, comfortably accommodating up to 8 guests. Enjoy a fully equipped kitchen, a spacious living area, and a private deck with access to a large yard, perfect for enjoying the outdoors.
Ski, Ride, Walk On/off Condo On Pico At Killington - Rutland, VT
9.8 10 reviews

Ski, Ride, Walk On/off Condo On Pico At Killington

apartment, Killington
This two-bedroom, two-bathroom condo is located at the base of Pico Mountain in Killington, Vermont, offering ski-in/ski-out access and proximity to the Green Mountain National Golf Course and the Appalachian Trail.
The ground-floor unit features a rear patio, a fully equipped kitchen, convenient on-site parking, keyless entry, and sleeps up to six guests with access to a health club (fees may apply) including a swimming pool and gym.
Your Home Away From Home - Rutland, VT
9.9 682 reviews

Your Home Away From Home

apartment, Rutland
This Rutland apartment is conveniently located in a central area, close to mountains, lakes, hiking trails, restaurants, downtown, and medical facilities. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a full kitchen with a fridge, freezer, and microwave, along with amenities like air conditioning, parking, and high-speed Wi-Fi, ensuring a comfortable and convenient stay.

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.

Popular destinations

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.

Wonderful Condo Located Near The Pool And Hot Tub Highridge J6 - Rutland, VT
10 1 review

Wonderful Condo Located Near The Pool And Hot Tub Highridge J6

apartment, Killington
This Killington condo, located in the Highridge complex on East Mountain Road, offers ski-in/ski-out access to Killington Resort and proximity to base lodges, restaurants, and shops.
The one-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with dishwasher, and includes access to a swimming pool, jacuzzi, tennis court, and on-site fitness and game rooms, plus stunning mountain views.
Alpine Chalet Grill, Fire Pit, Pool, Gym, Cornhole - Rutland, VT
10 6 reviews

Alpine Chalet Grill, Fire Pit, Pool, Gym, Cornhole

apartment, Killington
This Killington vacation home offers easy access to Green Mountain National Forest, Pico Mountain at Killington Ski Resort, and the Golden Express Quad, all within a 10-minute walk.
The 1,630-square-foot property boasts four bedrooms, two bathrooms, and sleeps eight, featuring a fully equipped kitchen, in-house laundry, a fireplace, and outdoor barbecue grills, perfect for Killington getaways.
New! Smart 3br Basecamp W/ Hot Tub, Ac, Ev Charger & Flat Parking - Rutland, VT
No reviews

New! Smart 3br Basecamp W/ Hot Tub, Ac, Ev Charger & Flat Parking

apartment, Pittsfield
This renovated 2,100 sq ft condo is located in North Sherburne, Pittsfield, on the Killington-Pittsfield border, offering convenient access to Killington ski lifts within a ten-minute drive and bypassing resort traffic.
This spacious dwelling accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a private hot tub, a Level 2 EV charger, a well-equipped kitchen, and mini-split AC units in every room.
Snowden- Pool, Gym, Hiking, Fireplace! - Rutland, VT
10 5 reviews

Snowden- Pool, Gym, Hiking, Fireplace!

apartment, Killington
This Killington vacation rental is located at the base of Pico Mountain, offering ski-in/ski-out access and proximity to Killington Resort.
The 1,120-square-foot condo features three bedrooms, two bathrooms, a fully equipped kitchen, a fireplace, and a private outdoor space; it comfortably sleeps eight guests and is near the Paramount Theater, New England Maple Museum, Black Dog Sports, and Killington Adventure Center.

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.

Charming Country Getaway With View - Rutland, VT
10 28 reviews

Charming Country Getaway With View

apartment, Ira
This two-bedroom rental is located just 15 minutes from the city of Rutland, Vermont, nestled in a peaceful, rural setting. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property features a unique layout with a lofted bedroom, a walkout basement with a separate living space and bedroom, and a porch and patio. The apartment can comfortably accommodate up to four guests and offers amenities like a fully equipped kitchen, a fireplace, and a large lawn with a vegetable garden.
Pond View Cabin-rustic 2 Bedroom-sleeps 4 - Rutland, VT
9.9 18 reviews

Pond View Cabin-rustic 2 Bedroom-sleeps 4

cabin, Chittenden
Pond View Cabin is located in Chittenden, Vermont, a short drive from Chittenden Reservoir, Killington, and Rutland, offering easy access to outdoor activities and attractions. The cabin consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cozy cottage features a private bedroom with twin beds and a sleeping loft with a double bed and sitting area, comfortably accommodating up to four guests. Enjoy modern amenities like fast WiFi, a 50" Roku 4k TV, heat/air conditioning, and a well-equipped kitchen, while relaxing on the front sundeck overlooking the pond.
84 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Rutland, VT
10 2 reviews

84 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Killington
This slopefront condo offers ski-in/ski-out access at Pico Village, steps from the Golden Express lift, with a shuttle to Killington's main base and is located 0.8 miles from McGrath's Irish Pub.
This 890 sq ft, family-friendly apartment accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, fireplace, smart TV, and optional access to Pico Sports Center amenities including an indoor pool and gym.
Killington/ Rutland 2 Bedroom Cabin, Cabin #4 - Rutland, VT
10 7 reviews

Killington/ Rutland 2 Bedroom Cabin, Cabin #4

cabin, Mendon
This cabin is located in the mountains near Mendon, Vermont, just 3 miles from Pico Mountain at Killington Ski Resort and 6 miles from Pico Pond, making it ideal for outdoor enthusiasts. It has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The cabin offers 2 bedrooms and 3 bathrooms, accommodating up to 6 guests in a spacious 550 square feet. Enjoy amenities such as a fireplace, a private spa tub, a fully equipped kitchen, free Wi-Fi, and a terrace or balcony with garden access.

Best Rutland, VT vacation rentals with parking

Charming Farmhouse Retreat With Mountain View - Rutland, VT
9.7 7 reviews

Charming Farmhouse Retreat With Mountain View

gîte, Clarendon
Vermont Respite For Travelers - Self Check-in - Rutland, VT
9.7 12 reviews

Vermont Respite For Travelers - Self Check-in

apartment, Rutland
The Green Mountain Retreat - Rutland, VT
9.8 13 reviews

The Green Mountain Retreat

apartment, Rutland
Vermont Meadow House - Rutland, VT
No reviews

Vermont Meadow House

house, Ira

Popular Luxury Vacation Rentals in Rutland, VT

Discover ultimate relaxation in a luxury Rutland, VT vacation rental, where comfort meets a central, prime location.

Cozy 1 Bd With Private Entrance - Rutland, VT
No reviews

Cozy 1 Bd With Private Entrance

apartment, Rutland

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.

House ∙ 2 Bedrooms ∙ 6 Guests - Rutland, VT
10 3 reviews

House ∙ 2 Bedrooms ∙ 6 Guests

house, Rutland
Peaceful Pond View ~30 Mins To Killington - Rutland, VT
10 57 reviews

Peaceful Pond View ~30 Mins To Killington

apartment, Proctor
Cold River 2 Bedroom Loft - Rutland, VT
10 7 reviews

Cold River 2 Bedroom Loft

house, Clarendon
4br Killington Home Perfect For Families, Pet-friendly, Fireplace - Rutland, VT
No reviews

4br Killington Home Perfect For Families, Pet-friendly, Fireplace

house, Killington

Top-Rated Vacation Rentals with a Pool in Rutland, VT

Choose a vacation rental in Rutland, VT with a swimming pool for a proper workout or a leisurely dip right in the heart of the city.

Pico F305 - Rutland, VT
9.2 9 reviews

Pico F305

house, Killington
Cubscorner - Pool, Sauna, Gym, Close To Mountain! - Rutland, VT
10 6 reviews

Cubscorner - Pool, Sauna, Gym, Close To Mountain!

apartment, Killington
Cubscorner - Pool, Sauna, Gym, Close To Mountain! - Rutland, VT
9.3 3 reviews

Cubscorner - Pool, Sauna, Gym, Close To Mountain!

apartment, Killington
Ranch At Mendon Mt Orchards - Rutland, VT
9.8 279 reviews

Ranch At Mendon Mt Orchards

apartment, Mendon

Check Out Vacation Rentals with a Hot Tub in Rutland, VT

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Rutland, VT.

Forest Mountain Escape- Beautiful Mountaintop Escape In Mendon, Vt, 20 Min To Killington 14 To Pico, Home - Rutland, VT
9.9 57 reviews

Forest Mountain Escape- Beautiful Mountaintop Escape In Mendon, Vt, 20 Min To Killington 14 To Pico, Home

house, Mendon
Killington Escape For Summer- Hot Tub, Family Fun-minutes From Killington & Pico - Rutland, VT
8.4 5 reviews

Killington Escape For Summer- Hot Tub, Family Fun-minutes From Killington & Pico

apartment, Rutland
Winter Lore: Hot Tub, Game Room, Pet-friendly! - Rutland, VT
9.2 25 reviews

Winter Lore: Hot Tub, Game Room, Pet-friendly!

apartment, Mendon
Winding Way Chalet: Large Family Ski Home With Amazing Amenities! Hot Tub. - Rutland, VT
8.8 3 reviews

Winding Way Chalet: Large Family Ski Home With Amazing Amenities! Hot Tub.

apartment, Killington
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