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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 59 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, (206)
"Perfect get away. "
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!
Vermont Country Cottage (Near Village)
Exterior

Vermont Country Cottage (Near Village)

9.2 out of 10, Wonderful, (10)
"This cottage reviewed very well online and pictures were very accurate too. It was secluded and far from neighbors, fire house across the street but zero activity the whole weekend. The cottage had the amenities listed. It was neat and tidy, well equipped. Very confortable. Loved the wood stove. We used that and it was wonderful. Check in/out Instructions were easy to follow. The area was beautiful, peacefu and not too far away from groceries, food or beverages. Would definitely go...
The price is AED 643
AED 1,411 total
includes taxes & fees
16 Mar - 17 Mar
Vermont Country Cottage (Near Village)
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
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, (27)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
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, (27)
"Close to Bromley and StrattonWarm, cozy, clean cottage"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Cottage on the Creek
Back of the cottage showing the creek running alongside it.

Cottage on the Creek

9.4 out of 10, Exceptional, (20)
"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. "
Cottage on the Creek
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK
Property grounds

Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and neat. Very quaint and in the woods. We had a great time. Looking forward to doing it again in the near future. "
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK
Perfect Country Cottage
Front of the cottage

Perfect Country Cottage

9.6 out of 10, Exceptional, (78)
"Host was great! On top of everything involved with the trip. The house worked out great for our ski trip. "
Perfect Country Cottage
New York Vermont Border Cottage Getaway
Living area

New York Vermont Border Cottage Getaway

9.2 out of 10, Wonderful, (11)
"2nd stay here and everything is just right. Owner very responsive to all questions."
New York Vermont Border Cottage Getaway
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 375
AED 540 total
includes taxes & fees
24 Feb - 25 Feb
Peaceful Cottage Retreat
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, (113)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.
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
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 624
AED 1,201 total
includes taxes & fees
24 Feb - 25 Feb
Comfy Cottage in Historic East Poultney
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
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.
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
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
Weston Vacation Rental - Close to Ski Resorts!
Living area

Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!
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
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

Gorgeous Victorian-Style House w/ Hilltop Pool!
Rupert Vacation Rental | 6BR | 3.5BA | 4,000 Sq Ft | 2 Steps for Entry

Gorgeous Victorian-Style House w/ Hilltop Pool!

8.8 out of 10, Excellent, (29)
"The house was a perfect weekend getaway for a group of friends from the city. It was absolutely gorgeous and had everything we could need. We even got two feet of snow, so it was a magical Vermont experience! We would definitely go back and thank you!"
Gorgeous Victorian-Style House w/ Hilltop Pool!
Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,451
AED 1,803 total
includes taxes & fees
25 Mar - 26 Mar
Long Trail House at Stratton Mountain Resort
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.8 out of 10, Excellent, (22)
"Unit is very close to ski lift. Ski in / ski out was great!!!"
The price is AED 279
AED 1,057 total
includes taxes & fees
24 Feb - 25 Feb
Lovely ski-in/out condo steps from ski lift with trails and amazing views
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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