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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 Sweet Grove Street - Rutland, VT
9.7 277 reviews

Home Sweet Grove Street

apartment, Rutland
This Rutland apartment is located just one block away from downtown, making it easy to walk to restaurants, shops, and entertainment. It has earned excellent ratings for location, cleanliness, and overall user experience.
The rental offers 4 bedrooms and 1 bathroom, comfortably accommodating up to 9 guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, laundry facilities, and ample parking.
Comfortable In Town Apartment - Rutland, VT
9.5 86 reviews

Comfortable In Town Apartment

apartment, Rutland
This apartment is located in Rutland, a city with a rich history and culture. It has received excellent ratings for its location, cleanliness, and amenities.
The apartment has one bathroom and can accommodate up to six guests. It features a fully equipped kitchen with a fridge, freezer, and microwave oven. Guests can also enjoy free internet access. Pets are also welcome in this apartment.
4br Home | Walk Downtown Rutland + Trails - Rutland, VT
10 40 reviews

4br Home | Walk Downtown Rutland + Trails

apartment, Rutland
This four-bedroom, two-and-a-half-bathroom Rutland apartment offers convenient downtown access to shops, dining, and the theater, with easy driving distance to Pico, Killington, and Okemo ski resorts.
The spacious rental sleeps up to 12 guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, Wi-Fi, air conditioning, and parking.
Cozy Cape-style Home Near Killington, Vt - Rutland, VT
10 39 reviews

Cozy Cape-style Home Near Killington, Vt

apartment, Rutland
This Rutland, Vermont dwelling is located on a quiet dead-end street, offering proximity to shopping and dining, with Pico Mountain 8.5 miles away and Killington skiing 12 miles distant.
This pet-friendly apartment accommodates up to 8 guests with 3 bedrooms, 1 bathroom, and features air conditioning, internet, a kitchen, and parking, with a spacious yard for outdoor relaxation.

Best Rutland, VT vacation rentals with air conditioning

Cabin ∙ 2 Bedrooms ∙ 4 Guests - Rutland, VT
No reviews

Cabin ∙ 2 Bedrooms ∙ 4 Guests

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.
New Firepit, Great Location, Dog Friendly, Kitchen - Rutland, VT
9.9 189 reviews

New Firepit, Great Location, Dog Friendly, Kitchen

apartment, Mendon
This Mendon vacation home sits just 2.1 miles from the Green Mountain Rock Climbing Center and within 6 miles of both the Rutland Regional Medical Center and the Paramount Theater, making it a convenient base for exploring the area. Guests consistently rate the home excellent for its cleanliness, location, and overall experience.
The 950 square foot home has three bedrooms and one bathroom, comfortably accommodating up to five guests. The fully equipped kitchen includes a fridge, freezer, microwave oven, and a washing machine, while modern amenities such as free WiFi and a Smart TV ensure a comfortable and connected stay.
Proctor Stays - Rutland, VT
10 2 reviews

Proctor Stays

house, Proctor
Proctor Stays, a 19th-century house in Proctor, Vermont, is conveniently located 13 miles from Mount Horrid Observation Site and within easy driving distance of Pico Peak, Gifford Woods State Park, and Killington Peak.
This 1190-square-foot vacation rental boasts four bedrooms, two bathrooms, and accommodates up to 15 guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and a garden.
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.

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.

Killington Retreat | Deck-fire Pit-mountain Views! - Rutland, VT
9.2 5 reviews

Killington Retreat | Deck-fire Pit-mountain Views!

apartment, Clarendon
This Clarendon, Vermont vacation home sits within six miles of Green Mountain National Forest, Diamond Run Mall, and the Vermont State Fairgrounds, offering easy access to outdoor recreation, shopping, and entertainment. This two-bedroom, one-bathroom house comfortably sleeps four guests and includes a fully equipped kitchen, laundry facilities, a balcony, and a garden with barbecue grills.
Pico Mountain Condo C-307 - 1 Br, 1ba Steps To Pico Ski Slopes, Bus To Killington - Rutland, VT
9.3 3 reviews

Pico Mountain Condo C-307 - 1 Br, 1ba Steps To Pico Ski Slopes, Bus To Killington

house, Killington
Pico Mountain Condo C-307 offers ski-to-door access near Killington's Pico Peak (2.4 miles) and is 6.9 miles from Killington Peak.
This 900-square-foot one-bedroom condo sleeps seven, features a fully equipped kitchen, fireplace, balcony, fitness center access, and free Wi-Fi, plus accessibility features.
Feel The Real Vt! Lakes, Hikes, A Foodies Delight! - Rutland, VT
10 1 review

Feel The Real Vt! Lakes, Hikes, A Foodies Delight!

apartment, Proctor
This Proctor vacation home is located 0.6 miles from Dorset Quarry and within 6 miles of Wilson Castle and the New England Maple Museum, offering a quiet rural setting near popular attractions.
This 1190-square-foot house features four bedrooms, two bathrooms, and can comfortably accommodate eight guests, boasting amenities such as a fully equipped kitchen, in-house laundry, and a terrace.
Pico E205 - Rutland, VT
8.0 10 reviews

Pico E205

house, Killington
Pico E205 is located in Killington, just 2.1 miles from Pico Peak and 6.7 miles from Killington Peak, making it a convenient base for exploring the area's ski slopes. The vacation rental has received very good user, location, and excellent cleanliness ratings.
The house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. You'll enjoy amenities like free parking, Wi-Fi, a fully equipped kitchen, a terrace with mountain views, and easy access to Gifford Woods State Park.

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.

Killington/okemo, 7p Hot Tub, Mtn.views, Spacious! - Rutland, VT
9.8 237 reviews

Killington/okemo, 7p Hot Tub, Mtn.views, Spacious!

apartment, Rutland
This Rutland apartment is located near downtown, just a 5-minute drive away, and is within a 10-minute drive of hiking trails. It has excellent user, location, and cleanliness ratings. This spacious 4-bedroom, 2-bathroom rental can comfortably accommodate up to 12 guests. The apartment offers a variety of amenities, including two kitchens, two living rooms, a hot tub, a fire pit, a foosball table, a grill, a deck, a patio, a screened porch, a large backyard, and mountain views.
Luxury 7br/7ba Mountain Retreat With Sauna, Hot Tub, And Stunning Views - Rutland, VT
9.0 23 reviews

Luxury 7br/7ba Mountain Retreat With Sauna, Hot Tub, And Stunning Views

apartment, Mendon
This family-friendly vacation home is conveniently located in Rutland, just 6 miles from Pico Mountain, Green Mountain Rock Climbing Center, and Bucklin Trailhead, making it an ideal base for exploring the area's natural beauty. Guests have consistently rated this property excellent, praising its spaciousness, amenities, and comfortable atmosphere.
This 7-bedroom, 7-bathroom home can accommodate up to 22 guests, offering ample space for large families or groups of friends. The property features a sauna, a spa tub, a game room, a garden, and a tennis court, providing endless opportunities for relaxation, entertainment, and outdoor activities.
The Mendon Cottage - Charming Vermont Home Close To Pico, Ski Rental Deals! - Rutland, VT
No reviews

The Mendon Cottage - Charming Vermont Home Close To Pico, Ski Rental Deals!

house, Mendon
The Mendon Cottage is located in Mendon, Vermont, 4.1 miles from Pico Mountain and 8.6 miles from Killington Resort, offering easy access to skiing and Gifford Woods State Park (4.8 miles away).
This two-bedroom, two-bathroom vacation home sleeps up to 11 guests and boasts a fully equipped kitchen, in-house spa, fitness center, free Wi-Fi, and on-site parking.
Ground Floor Entry With Ski In/out Access To Pico & Free Shuttle To Killington - Rutland, VT
10 33 reviews

Ground Floor Entry With Ski In/out Access To Pico & Free Shuttle To Killington

apartment, Killington
This one-bedroom apartment is located just a mile from Pico Mountain at Killington Ski Resort, perfect for a ski vacation. It has excellent user ratings and is family-friendly, allowing pets.
The 590 square foot apartment comfortably accommodates up to four guests with a full kitchen, a fireplace, and a private terrace. Enjoy the on-site amenities like the indoor pool, fitness center, spa tub, and garden, all perfect for relaxing after a day on the slopes.

Best Rutland, VT vacation rentals with parking

The Bunk House! Modern, Self Check-in - Rutland, VT
9.8 33 reviews

The Bunk House! Modern, Self Check-in

apartment, Rutland
Jack S`bearo- Ac, Pool, Mountain Views, Hiking, Gym - Rutland, VT
10 15 reviews

Jack S`bearo- Ac, Pool, Mountain Views, Hiking, Gym

apartment, Killington
Pico C202 Located At The Base Of Pico Mountain With Access To The Fitness Center. - Rutland, VT
9.6 7 reviews

Pico C202 Located At The Base Of Pico Mountain With Access To The Fitness Center.

apartment, Killington
Tinys Getaway - Rutland, VT
9.8 62 reviews

Tinys Getaway

apartment, Rutland

Popular Luxury Vacation Rentals in Rutland, VT

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

Killington Escape - Rutland, VT
9.7 60 reviews

Killington Escape

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.

Cortina Mountain Chalet - Outdoor Hot Tub - Close To Pico And Killington Mountains Home - Rutland, VT
9.4 22 reviews

Cortina Mountain Chalet - Outdoor Hot Tub - Close To Pico And Killington Mountains Home

house, Mendon
Winter Lore: Hot Tub, Game Room, Pet-friendly! - Rutland, VT
9.6 51 reviews

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

apartment, Mendon
Ski-on Ski-off At Pico Mtn Premier Slopeside House Rental. Dog Friendly!!! - Rutland, VT
10 10 reviews

Ski-on Ski-off At Pico Mtn Premier Slopeside House Rental. Dog Friendly!!!

apartment, Killington
Couples Retreat Near Killington With Hot Tub - Rutland, VT
9.8 18 reviews

Couples Retreat Near Killington With Hot Tub

apartment, Mendon

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.

10 Mi To Killington | Ac | Four-season Retreat - Rutland, VT
9.7 12 reviews

10 Mi To Killington | Ac | Four-season Retreat

apartment, Mendon
85 M² Condo ∙ 1 Bedroom ∙ 4 Guests - Rutland, VT
No reviews

85 M² Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Mendon
Charming 2-bedroom Slopeside At Pico Mountain E304 - Rutland, VT
9.2 23 reviews

Charming 2-bedroom Slopeside At Pico Mountain E304

house, Killington
Pico Village Resort G301 Contemporary Style - Rutland, VT
9.2 52 reviews

Pico Village Resort G301 Contemporary Style

apartment, Killington

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.

Large Secluded Home Minutes To National Golf Club! - Rutland, VT
9.7 112 reviews

Large Secluded Home Minutes To National Golf Club!

apartment, Killington
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
214 M² House ∙ 4 Bedrooms ∙ 8 Guests - Rutland, VT
8.0 1 review

214 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Mendon
Wonderful One Bedroom Condo Located In Highridge Condominiums J6 - Rutland, VT
10 1 review

Wonderful One Bedroom Condo Located In Highridge Condominiums J6

house, Killington
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