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Compare 54 Cottages in Rupert with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded covered entry
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (200)
"A true joy, and a home away from home. This was our second time here and we loved it so much all over again. Would recommend to anyone looking for a romantic getaway with all the comforts of home. Minutes away from Manchester, a cute lil town for all those tourist tendencies. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
See how close this is to the water? Gas grill for your use.
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
10.0 out of 10, Exceptional, (13)
"Amazing stay! Great area and lovely house to stay in for the weekend. Linda was amazing and the place was really clean with everything we needed!"
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
Home with a spring-fed pond and mountain view.
Terrace/patio
Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (110)
"Very nice and cozy place to getaway for a few nights! Very close to Manchester and places to eat and things to do. Koi pond was very pretty and we enjoyed feeding them! Loved having coffee on the deck with a view of the mountains, before we went on our adventures! "
Home with a spring-fed pond and mountain view.
Cottage on Lake Saint Catherine
Dock your boat or borrow our kayaks and enjoy the lake.
Cottage on Lake Saint Catherine
10.0 out of 10, Exceptional, (8)
"Looking for a quiet getaway on a Lake in Vermont in the Poultney area, this is where you would like to be. Comfortable rooms and great Lake views."
Cottage on Lake Saint Catherine
New York Vermont Border Cottage Getaway
Living area
New York Vermont Border Cottage Getaway
9.4 out of 10, Exceptional, (9)
"Cute property minutes from VT and an easy drive to Castleton to visit our college student. Very clean property and loved the immediate hot water. Kitchen was also fully stocked with supplies. Only suggestion would be to put a larger more comfy couch in living room as the small couch was hard and too tiny for husband and i to sit together. Otherwise, a great stay and would definitely book again. "
New York Vermont Border Cottage Getaway
Vermont Country Cottage (Near Village)
Exterior
Vermont Country Cottage (Near Village)
10.0 out of 10, Exceptional, (8)
"The house was so well stocked and in a great location. We were inly there for less than 24 hours but it was cozy and comfortable and overall great vibes as soon as you walk in! "
The price is AED 459
AED 1,179 total
includes taxes & fees
23 Nov - 24 Nov
Vermont Country Cottage (Near Village)
Cottage on the Creek
Back of the cottage showing the creek running alongside it.
Cottage on the Creek
9.6 out of 10, Exceptional, (19)
"It was a cute and rustic cabin. There is a lot of room so you have space for more people. We had one issue but the owner was quite nice about it. "
The price is AED 441
AED 864 total
includes taxes & fees
24 Nov - 25 Nov
Cottage on the Creek
Cozy Country Cottage located in Greenwich, NY
Exterior
Cozy Country Cottage located in Greenwich, NY
10.0 out of 10, Exceptional, (37)
"My wife and I loved the place everything was well marked everything we needed was there we are planning on going back that is how much we loved it very cleaned and cozy"
Cozy Country Cottage located in Greenwich, NY
Quaint lakefront home with great views & full kitchen
Quaint lakefront home with great views & full kitchen
8.4 out of 10, Very Good, (21)
"The cabin was pretty clean when we got there and it was a beautiful view."
Quaint lakefront home with great views & full kitchen
Quaint, friendly cottage with lakefront location & water views
Quaint, friendly cottage with lakefront location & water views
9.4 out of 10, Exceptional, (57)
"Enjoyed the screened in front porch facing the Lake Recommend a new mattress for the double bed"
Quaint, friendly cottage with lakefront location & water views
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
"Great location, comfortable, and spacious. A great home base for a fly-fishing trip to southern Vermont!" - Taylor, *****
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
10.0 out of 10, Exceptional, (24)
"Enjoyed our stay! Great location! Would stay again!"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Comfy Cottage in Historic East Poultney
Exterior
Comfy Cottage in Historic East Poultney
10.0 out of 10, Exceptional, (4)
"The location was perfect for us, close to family. The cottage is beautifully renovated and was very ready for us to move in for an extended stay. We hated leaving that shower! There's plenty to do within a short distance ... so many little businesses and beautiful places to explore! Very quiet, we slept very well in our comfortable bed! I took many morning strolls, such a pretty little area!"
The price is AED 514
AED 1,082 total
includes taxes & fees
24 Nov - 25 Nov
Comfy Cottage in Historic East Poultney
Peaceful Cottage Retreat
Exterior
Peaceful Cottage Retreat
9.8 out of 10, Exceptional, (41)
"We enjoyed our stay. Nice country atmosphere. "
The price is AED 459
AED 624 total
includes taxes & fees
24 Nov - 25 Nov
Peaceful Cottage Retreat
Lake St Catherine Vermont Camp Rockytop
View from lakeside deck and dock.
Lake St Catherine Vermont Camp Rockytop
9.6 out of 10, Exceptional, (39)
"Always a great stay. Clean and comfortable."
Lake St Catherine Vermont Camp Rockytop
Historic Cottage- near Saratoga- on Summit Lake
Lake view and access
Historic Cottage- near Saratoga- on Summit Lake
10.0 out of 10, Exceptional, (14)
"We were visiting relatives in Argyle and Glens Falls. Good location for us. Thanks"
Historic Cottage- near Saratoga- on Summit Lake
Rustic Farm Cottage set in over 100 acres in beautiful rural Upstate New York.
Hummingbird Cottage
Rustic Farm Cottage set in over 100 acres in beautiful rural Upstate New York.
10.0 out of 10, Exceptional, (4)
"We (adult couple) stayed at Andelyn Farm’s Hummingbird Cottage for a full week in July 2024. It is a comfortable and adorably-furnished antique cottage but we essentially lived on the spacious back porch which is furnished comfortably for reading, snoozing, playing board games and enjoying meals and overlooks the grounds (and is great for watching the hummingbirds visit their feeder). Andy and Lyn were the perfect hosts — responsive and helpful but unobtrusive. Only downsides or caveats: it is...
Rustic Farm Cottage set in over 100 acres in beautiful rural Upstate New York.
Vermont Cottage • Sleeps Five • Spectacular Mountain Views • Bed and Breakfast
Nestled Cottage Surrounded With Nature
Vermont Cottage • Sleeps Five • Spectacular Mountain Views • Bed and Breakfast
10.0 out of 10, Exceptional, (75)
"Cottage was as described, from the beautiful wood floors and furnishings to its’ unique window trim. Super clean and comfortable. But what raised the barr on this rental that tickled my grits was the welcome reception into Kay and Glenn’s home each morning for breakfast. Kay is quite delightful and put out a breakfast each morning that was over the top. Glenn was at the ready with a welcoming coffee and great tips on everything from day trips to accessible biking routes. Would definitely spend...
Vermont Cottage • Sleeps Five • Spectacular Mountain Views • Bed and Breakfast
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Cottage charm! The Front Cottage at MeadowView
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
10.0 out of 10, Exceptional, (22)
"Meadow View Cottage is everything it is advertised as and more! There is so much attention to detail that I literally felt at home. Everything is just where one might look for it. The owner was thoughtful and helpful and we hope to stay again when we visit Dorset!"
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Lakefront Cottage w/Breathtaking Views! Hiking.PaddleBoat.Doc.Fishing.WiFi
Cottage Illusion
Lakefront Cottage w/Breathtaking Views! Hiking.PaddleBoat.Doc.Fishing.WiFi
9.4 out of 10, Exceptional, (55)
"This cottage on Lake Saint Catherine is perfect for a quiet getaway in a quaint Vermont town, especially if you love to fish or boat. The house has been updated with new kitchen features and a new shower. It has been stocked with a thoughtful supply of kitchen items and linens and was squeaky clean throughout. Sandy, the property manager, responded quickly to an issue we reported and seemed very committed to helping guests. The only drawback was the presence of thick milfoil in the water. We...
Lakefront Cottage w/Breathtaking Views! Hiking.PaddleBoat.Doc.Fishing.WiFi
Cozy Country Cottage
Exterior
Cozy Country Cottage
10.0 out of 10, Exceptional, (5)
"Absolutely amazing place to stay property owner was so nice and easy to get along with very gorgeous property looking forward to staying again!! "
Cozy Country Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
10.0 out of 10, Exceptional, (158)
"A beautiful home in a beautiful setting, off the beaten track but not that far from many delightful areas. Kept immaculately clean, every aspect of this property is comfortable, cozy, and welcoming. Communication with the owners is easy and efficient, with response received very quickly."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!
Sit by the fire and then take a dip in the pool!
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!
9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Living area
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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