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Compare 70 Cottages in Rupert with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (209)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Peaceful Cottage Retreat

9.8 out of 10, Exceptional, (41)
"We enjoyed our stay. Nice country atmosphere. "
Peaceful Cottage Retreat

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

10.0 out of 10, Exceptional, (28)
"Great spot for a small family. Three adults and two kids stayed for a couple nights. Nicely furnished and very clean."
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

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

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

Dog friendly lakefront home w/fireplace near Lk George. 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!"
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Vermont Country Cottage (Near Village)

9.2 out of 10, Wonderful, (10)
"Cute place. Enjoyed our stay. "
Vermont Country Cottage (Near Village)

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

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"Enjoyed our stay! Great location! Would stay again!"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (116)
"The house was so well stocked with food, snacks, linens, the best quality paper towels, even toothpaste! Jeremy thinks of every detail. We stayed here when we skied Bromley which was a 17 min drive. Easy peasy. Jeremy is an excellent host. "
Home with a spring-fed pond and mountain view.

Quaint, friendly cottage with lakefront location & water views

9.4 out of 10, Exceptional, (57)
"Great access to lake."
Quaint, friendly cottage with lakefront location & water views

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

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"The cottage was great and the hosts very communicative and checking in to make sure we were all set. We will be hopefully making this a yearly trip as we loved the seclusion and beautiful area. "
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

Quaint lakefront home with great views & full kitchen

8.4 out of 10, Very Good, (21)
"Place was exactly as described! Great escape at a lake!"
Quaint lakefront home with great views & full kitchen

Comfy Cottage in Historic East Poultney

10.0 out of 10, Exceptional, (6)
"The cottage had everything we needed to make our vacation perfect. It was well located to Ski Killington and Stratton. The host live right next door and was very responsive for all our needs to make the stay as pleasant as possible. We would definitely rent again."
The price is SAR 563
SAR 1,155 total
includes taxes & fees
30 Apr - 1 May
Comfy Cottage in Historic East Poultney

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

Historic Cottage- near Saratoga- on Summit Lake

10.0 out of 10, Exceptional, (14)
"Overall it was great! Very nice and helpful hosts and great lake views!"
Historic Cottage- near Saratoga- on Summit Lake

Rustic Farm Cottage set in over 100 acres in beautiful rural Upstate New York.

10.0 out of 10, Exceptional, (4)
"We were visiting family in Vermont for the forth of July. Hummingbird Cottage was charming and fit the needs of our group of 4 perfectly. We especially enjoyed the large back porch which was comfortable, inviting and perfect for enjoying morning coffee or evening cocktails. Hosts were quick to respond and very accommodating."
Rustic Farm Cottage set in over 100 acres in beautiful rural Upstate New York.

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
8.0 out of 10, Very Good, (2)
"This was the perfect place for 2 people to stay for a trip to Okemo. Everything we could have needed was available on the property, it was very clean and comfortable, and the hostess was great at communicating details ahead of time. Thanks for allowing us to use your property - I would love to return!"
Idyllic Wallingford Retreat - Near Skiing & Hiking

Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont

10.0 out of 10, Exceptional, (2)
"We had the BEST time on our short little getaway to the Vermont mountains! We are very familiar with the area but this was our first VRBO. We didn’t really know what to expect but Lizzie’s place was absolutely perfect for our family of 5 (kids ages 2,5 and 7.) The space was cleaner than clean (which is a big deal to us) and updated. It is such a cute and happy little place and we didn’t want to leave. The kids loved the bunk beds, and the rooms couldn’t have been more comfortable and well...
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
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

10.0 out of 10, Exceptional, (166)
"This was our second Thanksgiving at Creekside Camp. Once again, we had a wonderful stay. Not enough can be said about this charming and cozy cabin. Dan and Kellie do a phenomenal job as hosts and managing the property. We highly recommend a stay in this rustic, yet highly appointed property!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "
The price is SAR 759
SAR 2,416 total
includes taxes & fees
1 May - 2 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (209)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.