Holiday rentals in Rupert

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Top-rated holiday rentals in Rupert

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Wilmington

5 out of 5 average rating, 8 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Enjoy stunning lake & mountain views w/ easy access to hiking, swimming, boating, & fishing (kayaks, paddle board, and bikes included). Cathedral ceilings w/ beams provide a cozy feel & heated floors give an always-warm home in the winter. Covered deck w/ grill is great for outdoor dining. Additional features include outdoor hot tub, sauna, & quality game room (pool table, shuffleboard, foosball, ping pong). 4WD/AWD required in winter. Close to Mt. Snow & downtown Wilmington w/ shops and dining.

Superhost

Cabin in Lake George

4.85 out of 5 average rating, 124 reviews

Spacious Lake George Lodge -Near West & Gore Mnt

SignatureRetreatsNY.com Book your Signature Retreat today and enjoy this Lake George Log Mansion Lodge. This Spacious 2836 sqr ft retreat, w/ 4 bedrooms, 7 beds and 3 full bathrooms is located at the foothills of French Mount. It has the Best of both worlds-an Amazing Adirondack Custom Log Cabin and Update Modern Amenities with Cozy Home Comforts. Located centrally to Lake George, the MillionDollar Beach, the Adirondacks, Glen Lake, West Mountain, Gore Mountain, Six Flags & Saratoga Springs.

Guest favourite

Home in Lake Luzerne

4.98 out of 5 average rating, 128 reviews

River Cottage

Beautiful cottage in the Adirondack Mountains situated on over an acre of waterfront property with River access. Enjoy swimming, Kayaking and fishing on the Hudson River, all right from the backyard of the house. It has a great deck which overlooks the river with perfect views for enjoying sunset cocktails… Yard also has two fire-pits for night time fun and laughs. Cabin is close to skiing, snowmobiling trails. Perfect for a family getaway to make awesome memories. STAY, SPLASH, SMORES!!!!!

Guest favourite

Home in Hadley

5 out of 5 average rating, 50 reviews

The Summit on The Sacandaga is sure to Satisfy.

We are excited to share our Gem with YOU! If you are looking for a Lake House on a private Mountain Top, we’ve got you covered! Our Chalet has been COMPLETELY remodeled & freshly furnished in 2022! This place is oozing vacation vibes! We too love travel & adventure, so we are pretty sure we know what you need! Morning coffee on the deck overlooking 285’ of private beach or cocktails on the dock or fireside. Bring your boat or enjoy our paddle boat, kayaks, canoe & hammocks... Be our guest!

Guest favourite

Flat in Wilmington

4.91 out of 5 average rating, 129 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Guest favourite

Home in Chestertown

5 out of 5 average rating, 14 reviews

Adirondack Home 15 minutes from Gore

Located between Gore and Lake George. Newly renovated 4 bedroom 2.5 bathroom, beautiful property with a private beach and salt water pool Local attractions: Gore Mountain 13 miles Lake George 20 miles Loon Lake beach 1 mile Lake Placid 60 miles Schroon Lake 12 miles Brant Lake 7 miles Six Flags 25 miles Short distance to local hiking trails, snowmobile trails, fishing spots, horseback riding, boating and more. Lots of amazing local restaurants, distilleries, and breweries to try out.

Guest favourite

Cabin in Lake George

5 out of 5 average rating, 39 reviews

Great location. Walk to Village attractions/beach!

Our stylish Adirondack log cabin is the perfect location for your Lake George four season getaway. Steps away from Million Dollar Beach, restaurants and the Village. Easy access to snowmobile trails and thirty-five minutes to Gore Mountain for skiing. Close to Adirondack High Peaks and local hiking trails. Smart TVs in each bedroom, living room and den. Two Vermont cast iron gas stoves. Fire pit, outdoor seating and garage to park your car or store your winter toys. Filtered lake views.

Guest favourite

Flat in North Creek

4.92 out of 5 average rating, 61 reviews

The Rail house

You will enjoy easy access to everything from this centrally located place. Just off Main Street Walking distance to everywhere Supermarket across the street Spirit store in same plaza. Walk along the beautiful Hudson River And browse local gift shops right in Main Street. Option for third person with a cot only sleeper for an additional charge of $50 A visit to Gore mountain is just a few short minutes away drive. Private guest walking trails to the Hudson and walking path.

Guest favourite

Flat in Pittsford

4.97 out of 5 average rating, 30 reviews

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

Guest favourite

Guest suite in Lake George

4.95 out of 5 average rating, 74 reviews

Lake George Perfect Location

Lake George premier location with your own entrance and parking spot for this newly renovated VERY clean Bedroom, Amenity Stocked Kitchen and Bathroom and washer and dryer. Easy lake access that is just steps from our back deck to private access to the lake for you to sunbath, swim or launch our included kayaks. Perfectly located for all seasonal activities. Walk to three local favorite restaurants. Just a few minute drive to Lake George Village.

Superhost

Cottage in Lake George

4.75 out of 5 average rating, 84 reviews

Renovated Cottage in Lake George

Enjoy this cozy cottage in Adirondack style with mountain view right in front! Completely remodeled in 2018, cottage is on US route 9 just a mile straight away from Lake George village! Perfect for remote work with 200mbps internet. Town has activities like boat rentals, ferry, lunch/dinner at restaurants by the lake! For kids there's arcade, mini golf, go karts, laser tag and more just 10-15mins away! 30mins drive to skiing mountains in winter.

Guest favourite

Home in Cavendish

4.96 out of 5 average rating, 23 reviews

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!