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Rupert Pet Friendly Holiday Rentals

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    Don't let other travellers get your favourite Rupert area holiday rental. You're so close to securing your perfect getaway. Book today.
    20 Matching Rentals in the Rupert AreaView all 36 rentals
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    HICKORY RIDGE VERMONT LOG CABIN1 / 26
    (20)Excellent
    Rupert
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Rupert
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    The following rentals are within 15 kilometres of Rupert.
    Five Bedroom Secluded Ski House Located Two Miles From Downtown Manchester1 / 19
    (2)Excellent
    Manchester
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Newly Renovated Luxury Colonial close to everythin1 / 23
    (3)Excellent
    Manchester
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Grill
    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2017
    I can't speak too highly of this lovely house. Extremely comfortable and tastefully furnished and the surroundings are gorgeous with plenty to do in Manchester and further...
    Reviewed 25 August 2017
    This a beautiful house, with stunning views over the valley, in a great location just outside Manchester. It is immaculate, and equipped with everything you might need for a...
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    About this property
    Newly renovated home, with top of the line kitchen. Master bedroom retreat. A living room on both floors for entertaining. Open plan living on second floor. Central Air Conditioning. Stone fireplaces. Laundry onsite. Spectacular views from every window. Only a five minute drive from the center of...
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    Manchester, Green Mountains 05255
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pond Mountain Inn: Garden Cottage1 / 18
    (11)Excellent
    Wells
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Mountain Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2017
    We stayed with Glenn and Kay over the Thanksgiving holiday in the Loft apartment, which was lovely. It is very large with a full kitchen, wonderful art and antiques and...
    Reviewed 28 September 2015
    My husband and I stayed at the cottage for a few days in September 2015. The accommodations were amazing. The cottage is spacious, comfortable and quiet with all the comforts...
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    About this property
    2 Bedroom Cottage, 1 Bath, Sleeps 5 Sunsets over Pond Mountain flood the cottage brilliantly through large western-facing windows situated in the slim pillars of the pines that provide peace and tranquility and fresh air which is uniquely Vermont. Garden Cottage Amenities Full American Breakfast...
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    Location Information
    Wells, Vermont 05774
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Sunsets, mountain and meadow views, Hildene Farm, 4 min. to the Equinox Resort1 / 30
    (1)Excellent
    Manchester
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Patio
    • Hot Tub
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2016
    This property greatly exceeded our expectations…what a beautiful Home! A stay here is the perfect way to experience New England. My husband and I are familiar with this part...
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    About this property
    For your Vermont get-away, a wonderful home away from home, welcoming, cozy, comfortable, with luxury details, and sited on the most impressive location in Manchester Village. The house abuts and overlooks the protected 40 acre Hildene Meadow, with mountain views, and gorgeous sunsets. Our home is...
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    Manchester, Green Mountains 05255
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Pond Mountain Inn: Loft Apartment Suite1 / 17
    (22)Excellent
    Wells
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Mountain Views
    • Washer
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    We stayed a week at the cottage. It was our fourth time at Pond Mountain Inn! We discovered new hiking trails with breathtaking views nearby. Lake St Catherine is also a great...
    Reviewed 3 April 2017
    My wife and I enjoyed a stay at this lovely Bed and Breakfast. The accommodations were beautiful. This is not your average b n b. Full Kitchen and living room in the loft. It's...
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    About this property
    Panoramic sunrise views come alive with champagne light in this rustic, deeply comfortable spacious suite with accented reclaimed Maine barn timbers and beamed vaulted ceiling feels like a cabin in the woods. Loft Apartment Amenities Queen Bed & Pullout Queen Bed with 300 Thread Count 100%...
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    Location Information
    Wells, Vermont 05774
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Manchester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly in the middle of Manchester the house is close to all restaurants,stores,ski mountains, lakes, and horse show. A very spacious home ( 1866 sqft ) 3 large bedrooms 2 full bathrooms , deck, backyard ,and plenty of on site parking;fully stocked kitchen. Home is perfect for families and...
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    Location Information
    Manchester, Green Mountains 05255
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Manchester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    • Patio
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy STUNNING views of Mount Equinox in three directions. There are 5 bedrooms, 7 beds, 2 full baths and one half bathroom. This is not your basic white-walled house - the rooms are painted with murals, faux-marbling, and fantastic tile work. Enjoy the nightly sunset from the Venetian tiled...
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    Location Information
    Manchester, Green Mountains 05250
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    RYE CHALET IN HIDDEN VALLEY. Spectacular views. Vermont's famous fresh air.1 / 22
    (2)Excellent
    Wells
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Central Heating
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2017
    Wonderful Wonderful Wonderful !! My guests and I had an amazing stay at this beautiful chalet! The views are stunning and the home was so clean! Would recommend to everyone and...
    Reviewed 19 October 2012
    We just came back from Wells Vermont, we stayed at the Rye Chalet for three nights. The chalet is very clean, there is 3 bedrooms and three bathrooms, washer and dryer, 2...
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    About this property
    Spacious and comfortable private home-turned-vacation-home offers a flexible floor plan suitable for small group getaways and large group gatherings. From the deck, view the faraway mountains, listen to the brook and take in the tranquility as only Vermont can offer. The perfect country retreat....
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    Location Information
    Wells, Vermont 05774
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    VERMONT COTTAGE ON THE LAKE1 / 26
    (7)Very good
    Wells
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    What an excellent place for family time. We got to spend time on the boat and on the dock. The owners were extremely helpful and accommodating. The cottage was very comfortable...
    Reviewed 28 May 2017
    We never actually stayed at the place due to change in plans but the owner were ever so helpful in meet our accommodation needs and with the pricing, we did how every stop by...
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    About this property
    BOOKING NOW FOR THE SEASON ( MAY , 2017 THROUGH SEPTEMBER 2017) WEEK TO WEEK FROM SATURDAY TO SATURDAY $1075 per week , $135 per night ,( except holidays ), holidays & weekends start at $185 per night $4200 per month. Sleeps six to eight people . A $300 security deposit is required. Non...
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    Location Information
    Wells, Vermont 05774
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    East Dorset
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Washer
    • Internet Access
    • Parking
    • DVD Player
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Over looking the Battenkill our home is on a private road 10 minutes from Bromley, 20 minutes from Stratton and less than 5 minutes from Manchester outlets! We offer a perfect secluded vacation getaway with a front porch, large back deck and quiet atmosphere. Only minutes from area restaurants,...
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    Location Information
    East Dorset, Green Mountains 05253
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Manchester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This guest house boasts beautiful views of Mount Equinox and a field filled with Black-eyed Susans by late summer. The cozy interior with wood beam ceilings and a stone hearth will take you back to a simpler time while the back doors open up to a seasonal, fenced-in pool, as well as a gas grill...
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    Location Information
    Manchester, Green Mountains 05254
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Dorset
    8 Bedrooms, 4 Bathrooms, Sleeps 23 Quick View
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    Amenities & Details
    • Parking
    • Balcony
    • Mountain Views
    • Grill
    • Washer
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our fully furnished 8 bedroom 3.5 bath ski Clubhouse in East Dorset, VT is available for rent in April - November. The house was significantly renovated in 2016. We are just north of the Emerald Lake Park entrance (3-5 min walk) and 1.9 miles north of the VT Horse Show and Summer Festival. The...
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    Location Information
    Dorset, Green Mountains 05251
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 23
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    Boorn Brook Farm - Historic Renovated 1820's Barn - Skiing, Shopping, Relaxing1 / 13
    (2)Excellent
    Manchester
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 December 2017
    This historic barn is breathtaking, inside and out. Beautifully furnished in a truly stunning location, this is the perfect place for true relaxation. We particularly enjoyed...
    Reviewed 3 October 2017
    With all that is happening in our country, I found myself in a beautiful and warm community in Manchester Vermont. My sister and I were able to savor and appreciate the solace...
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    About this property
    Now the new home of Green Mountain Falconry School! Once the country estate and studio of famed painter and fly fishing enthusiast Ogden Pleissner, Boorn Brook Farm has been restored to its original splendor. Situated on 53 acres of open meadows and old apple orchards with stunning views, Boorn...
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    Location Information
    Manchester, Green Mountains 05255
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Manchester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Terrace
    • Balcony
    • Patio
    • Washer
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Manchester Village, this spectacular historic home was originally built in 1790 as a tavern and inn by Captain Peter Black. The inn was later purchased in 1837 by Rev. Dr. Joseph Wickham, legendary headmaster of Burr and Burton Academy. The home has since been renovated to...
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    Location Information
    Manchester, Green Mountains 05254
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Manchester
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Grill
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With convenient access to nearby mountain resorts, amenities such as a private game room and wood-burning fireplace, and all of the space that your friends and family could need, this luxurious, dog-friendly Manchester has everything you need for a memorable Vermont getaway! Shops, restaurants,...
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    Location Information
    Manchester, Green Mountains 05255
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Manchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Parking
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to scenic New England with a stay in this adorable two-story clapboard home. Adorned with a private deck, a beautiful sun room, and a superb location just steps from the golf course, this dog-friendly Manchester vacation rental is a welcome retreat any time of the year. The house is tucked...
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    Location Information
    Manchester, Green Mountains 05254
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    East Dorset
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Terrace
    • Grill
    • Washer
    • Mountain Views
    • Balcony
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PERFECT LOCATION IN THE MIDDLE OF GOLDEN TRIANGLE OF SKI COUNTRY. SECONDS FROM THE APPALACHIAN TRAIL HEAD. THIS SPACIOUS WARM WOODSY MODERN MOUNTIAN RETREAT WITH HOT TUB IS IN THE HEART OF THE GREEN MOUNTAIN FOREST AND CLOSE TO MANCHESTER SHOPPING, DORSET QUARRY, STRATTON MOUNTAIN, SECONDS TO...
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    Location Information
    East Dorset, Green Mountains 05340
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Dorset
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a secluded vacation rental in New England with loads of old world charm, consider a stay at this three bedroom Dorset home in the forest with a wood-burning fireplace, porch, and patio. What's nearby: This home is located within walking distance of downtown Dorset for quaint...
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    Location Information
    Dorset, Green Mountains 05251
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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