Vacation rentals in Rupert

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Top-rated vacation rentals in Rupert

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Guest favorite

Guest suite in Dorset

4.88 out of 5 average rating, 147 reviews

Guest Suite in historic 1804 tavern, w/ Breakfast.

You'll have the whole 3rd floor to yourself with a new private bath, large bedroom with a/c, and a sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has resulted in beautifully decorated historic home. You'll have a continental breakfast in the house's original dining room. We're a four a minute drive from the center of historic Dorset village, which has excellent restaurants, a cafe, and a general store.

Sep 17 – 24

R2,568 ZAR per night

Guest favorite

Home in Granville

4.85 out of 5 average rating, 152 reviews

Home by the Mettowee River- Simply the best!

Located near the Mettowee River in the village of historic Granville New York, this home will be the perfect place for your stay. More spacious and affordable than any hotel, this simple home allows you to enjoy the comforts of "home away from home". Ideally situated an hr drive from Vermont mountains and skiing, and a short drive from Lake George, this home is well- suited for vacationing or family trips. We look forward to having you stay when you come to the lovely village of Granville.

Sep 18 – 25

R1,905 ZAR per night

Guest favorite

Apartment in Dorset

4.99 out of 5 average rating, 178 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Jan 17 – 24

R3,120 ZAR per night

Guest favorite

Apartment in Manchester

4.99 out of 5 average rating, 147 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

May 5 – 12

R1,666 ZAR per night

Guest favorite

Guest suite in Manchester

4.89 out of 5 average rating, 119 reviews

Bright Manchester Studio with Sleeping Loft

Our studio apartment with sleeping loft is great for two adults or a couple with children. Located on a quiet country road great for taking long walks. There is a queen bed in the loft and a pull out queen sofa in the living area. Bright with high ceilings and all new furnishings. We are less than three miles from town, 20 minutes to Bromley and 25 minutes to Stratton. Close to hiking, biking, fishing, great restaurants and shopping. Please note;Owners lives on premise in main house.

Aug 30 – Sep 6

R3,380 ZAR per night

Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 785 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Feb 23 – Mar 2

R1,975 ZAR per night

Guest favorite

Apartment in Middletown Springs

4.88 out of 5 average rating, 204 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

May 7 – 14

R1,359 ZAR per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 588 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Oct 26 – Nov 2

R2,603 ZAR per night

Guest favorite

Cabin in Granville

4.98 out of 5 average rating, 133 reviews

Quaint log cabin nestled in the woods

Enjoy a break from the daily grind at this lovely tiny log cabin nestled among beech and ash trees. This tiny cabin provides peace and quiet on nearly 4 wooded acres just minutes from the town of Granville, NY. A full kitchen, living room, one bathroom and a loft bedroom complete with stackable washer/dryer provide a place to relax and soak in nature. The spacious front porch grants a protected outdoor space to watch the wildlife and enjoy the fresh air with your family and pup.

Jan 17 – 24

R2,241 ZAR per night

Superhost

Cabin in Sandgate

4.92 out of 5 average rating, 127 reviews

Vermont Mountainside Cabin- Nature + Epic Views

PLEASE READ THE FULL DESCRIPTION, & FEEL FREE TO GET IN TOUCH WITH ANY QUESTIONS - THANKS This cozy, mountainside cabin is the perfect place to relax and reconnect with friends, family, and nature. The house is nestled in the heart of the Green Mountains, and feels a world away from the hustle and bustle of everyday life. And if you feel like driving to town, our corner of southern Vermont offers a host of outdoor recreation, dining, arts, and more.

Sep 5 – 12

R3,032 ZAR per night

Guest favorite

Cabin in Wells

4.95 out of 5 average rating, 151 reviews

Gatsby's Getaway

Ready to disconnect and recharge? Welcome to Gatsby's Getaway! Watch the sun rise over the Green Mountains and Little Lake from the comfort of your deck. If the weather doesn't agree, enjoy your morning coffee in front of the cozy fireplace in your charming bungalow, complete with cathedral ceilings and sliding glass doors. Close to tons of hiking & biking trails, and outdoor activities. 10 minutes to nearby Granville, NY or Poultney, VT.

Sep 29 – Oct 6

R2,261 ZAR per night

Guest favorite

Apartment in Poultney

4.94 out of 5 average rating, 306 reviews

Cozy Poultney Village Apartment

We enjoy booking our two-story in-law apartment with a private entrance that is attached to our 1850 Poultney Village home. We are located a block away from Main Street with shops, books, and eateries. We are in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We are also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Jan 15 – 22

R1,545 ZAR per night