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Pet Friendly Vacation Rentals in Pittsfield and nearby

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    From
    $428
    / Night
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    1 / 8
    Pittsfield
    3 Bedrooms / 2 Bathrooms / Sleeps 20
    Overview Make Enquiry

    The following rentals are within 15 kilometres of Pittsfield, Vermont.

    From
    $274
    / Night
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    1 / 20
    5 of 5 stars (1) Excellent
    Barnard
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    From
    $243
    / Night
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    1 / 16
    4.5 of 5 stars (2) Very good
    Rochester
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    From
    $264
    / Night
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    1 / 26
    4 of 5 stars (1) Very good
    Killington
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Mountain Views
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Winter, spring, summer and fall, there is always something to do and something to fall in love with at this cozy Vermont vacation home. Kids will love the rustic sturdy bunkbeds and folks just love to relax in front of the fire cozying up to good book. There are many downhill and cross country ski... View all property information
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    4 of 5 stars Reviewed 25 August 2014
    WE chose this rental house because of its 5 minute walk to the Long Trail Brewery. Hubby and I and another couple and their 2 pre-teen daughters went to the 25th Anniversary...
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    From
    $246
    / Night
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    1 / 19
    5 of 5 stars (1) Excellent
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Microwave
    • Sauna
    • Stereo System
    • Gym
    • Hairdryer
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The best Ski-on-Ski-off location, imagine walking off your back deck and the trail is right there. This condo has it all, great location, Sunrise amenities and very is comfortable. The master bedroom has it's own bathroom with a big sunken jetted tub big enough for two. The master also has a queen... View all property information
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    5 of 5 stars Reviewed 31 January 2015
    This is really ski on ski off. We were not disappointed. The space was clean, well stocked kitchen and nice linens.
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    From
    $456
    / Night
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    1 / 10
    5 of 5 stars (8) Excellent
    Killington
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Mountain Views
    • Satellite TV
    • Water Views
    • Refrigerator
    • Cooker
    • DVD Player
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    The Dew Drop Inn, Winter Ski House is Charming & Cozy. It is in the valley surrounded by Scenic Mountain Views. There is an Outdoor Hot Tub in the back of the house. It is 1 mile from Killington's worlds famous high speed 'Skyeship Base Lodge GONDOLA' (8 passenger- hi speed Gondola that takes... View all property information
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    5 of 5 stars Reviewed 27 February 2015
    Thank you so much for letting us stay at The Dew Drop Inn! It was such an amazing time and everyone had only the best things to say about your place. It was even better than...
    5 of 5 stars Reviewed 23 February 2015
    The property is clean, well maintained and very comfortable; the showers are hot and powerful, the fire is toasty and the hot tub is great. There was plenty of room for 10...
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    From
    $280
    / Night
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    1 / 27
    5 of 5 stars (1) Excellent
    Killington
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Gym
    • Sauna
    • Hot Tub
    • Balcony
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Views of the ski trails form your bedroom window at this conveniently located 3 bedroom 2 bath condo which is across the street from the lifts! Comfortably sleeps 6-8, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts,... View all property information
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    5 of 5 stars Reviewed 15 April 2015
    We're a group of working professionals from NYC and ATX and loved our stay. Everything was included and it was very homie. Thanks again.
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    From
    $365
    / Night
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    1 / 73
    5 of 5 stars (2) Excellent
    Killington
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Microwave
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Life doesn't get any better! Sit and relax or ski/ride at the best resort and mountain that New England offers. You should try the Sunrise Mountain Village High Mountain Back-country offering (snowshoeing and cross-country skiing out your door, with dining options) right in our community and dining... View all property information
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    5 of 5 stars Reviewed 24 February 2015
    Excellent 3 days of skiing from this ski out/in tastefully decorated and outfitted ski condo (55 or 60 " HDTV and excellent Wi-fi). Short walk to the end of the trail to access...
    5 of 5 stars Reviewed 5 February 2015
    This was the perfect spot for us! We love Killington and never stayed there on a ski on ski off before. We had a group of 8 and 2 dogs so there were not many options for that and...
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    From
    $156
    / Night
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    1 / 7
    1 of 5 stars (1) Terrible
    Killington
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Sauna
    • Stereo System
    • Hairdryer
    • Gym
    • Balcony
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Spacious Studio condo located in Building 2 with great mountain views! This unit sleeps 2- 4 and is 'pet friendly'. It is conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants and... View all property information
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    1 of 5 stars Reviewed 20 February 2015
    My wife and I stayed in this unit and heating was terrible! The heat never got above 56 degrees. The maintenance guy told me this was problem in past and owner needs to...
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    From
    $321
    / Night
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    1 / 32
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Terrace
    • Stereo System
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Getaway and enjoy yourself at this Green Mountain Vermont Chalet located in Stockbridge, VT near Killington Ski Resort. The views are breath taking at our secluded home. Cedar Rock has a large stone fireplace and a new outdoor Hot Tub to enjoy with friends and family. Our home is at the end of the... View all property information
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    From
    $199
    / Night
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    1 / 24
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Sauna
    • Microwave
    • Gym
    • Mountain Views
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Quite, great views, close to everything and across the street from the lifts! Comfortably sleeps 4-6, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants... View all property information
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    From
    $158
    / Night
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    1 / 18
    Killington
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Microwave
    • Gym
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Newly renovated condo across the street from the lifts! Comfortably sleeps 2-4, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants and night clubs. The... View all property information
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    From
    $199
    / Night
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    1 / 27
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Terrace
    • Microwave
    • Stereo System
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Newly updated condo across the street from the lifts! Comfortably sleeps 4-6, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants and night clubs. The... View all property information
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    From
    $212
    / Night
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    1 / 37
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Sauna
    • Balcony
    • Hot Tub
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Bright and spacious condo across the street from the lifts! Comfortably sleeps 4-6, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants and night clubs.... View all property information
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    From
    $151
    / Night
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    1 / 27
    Killington
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Stereo System
    • Balcony
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    EZ Access 1 bedroom 1 bath condo across the street from the lifts! Comfortably sleeps 2- 4, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants and night... View all property information
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    From
    $237
    / Night
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    1 / 20
    Killington
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Sauna
    • Shared Outdoor Pool...
    • Deck
    • Fireplace
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a perfect place for you and your family pet. This tri-level (sunken living room level) condo is sure to please. There is a small deck with a grill with a small pond in the back. This property is the first cul-de-sac as you enter the Woods Resort. This a short walk to the main entrance for... View all property information
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    From
    $182
    / Night
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    1 / 27
    Killington
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Sauna
    • Mountain Views
    • Gym
    • Balcony
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Views of the ski trails right outside your enclosed porch! Comfortably sleeps 2-4, we are 'pet friendly' conveniently located at the top of the Killington Access Road, steps to Killington's Snowshed Lodge & lifts, Killington snow tubing park, Killington Golf Course, restaurants and night clubs. The... View all property information
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    From
    $238
    / Night
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    1 / 41
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Gym
    • Sauna
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Welcome to your home away from home. Outside in the brisk winter air, you are surrounded by white peaks spotted with skiers on the slopes. In the summer, you are soothed by the rolling lush green hills, fresh pine smells and chattering birds. And in the fall, there is no place else where the colors... View all property information
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    From
    $249
    / Night
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    1 / 25
    Killington
    3 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Hot Tub
    • Wi-Fi
    • Deck
    • Dishwasher
    • Gym
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nicely decorated three bedroom townhouse tucked away on the upper level of the Woods Resort is surrounding by the trees for that feeling of being away from it all. This tri-level town house offers a back deck with a grill for your enjoyment. Have a family pet? No worries, this townhouse is pet... View all property information
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    From
    $152
    / Night
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    1 / 11
    Amenities & Details
    • Dishwasher
    • Microwave
    • Fireplace
    • Towels Provided
    • Parking
    • Paper Towels...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    2 Bedroom Economical Valley Park Condo (sleeps 6). This the right vacation resort for you in this great economic crisis. You must seek something which can fit into your budget, and Valley Park is it! Wood Burning Fireplace, 5 Miles From Ski Area, Perfect for an affordable family vacation. Main... View all property information
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    From
    $943
    / Night
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    1 / 19
    Killington
    7 Bedrooms / 3 Bathrooms / Sleeps 25
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Dryer
    • Parking
    • Towels Provided
    • Hot Tub
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This very spacious two level house, with plenty of country farmhouse charm, is conveniently located to restaurants and the night life as well as the Killington Ski Area. outside hot tub, pool table, 42' flat screen TV, in addition to new beds, bedspreads, and drapes. The fully equiped kitchen has... View all property information
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    1 / 8
    Killington
    3 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Gym
    • Shared Outdoor Pool...
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Parking
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a three bedroom, tri-level (sunken living room level) condo is sure to please you and your family. Do you have a family pet? Bring your family pet along as this condo is pet friendly, (see below for pet notes) . There is a small deck with a grill that overlooks a small pond. This property... View all property information
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    1 / 6
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • DVD Player
    • Linens Provided
    • Gym
    • Towels Provided
    • Deck
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This second floor, one bedroom loft property with balcony, is tastefully decorated and sure to make you feel at home. The main level includes the kitchen fully equipped with a refrigerator, stove, microwave, dishwasher, toaster, coffee pot, blender, breakfast counter with four stools, and... View all property information
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    1 / 16
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Parking
    • Hot Tub
    • Gym
    • Deck
    • Fireplace
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rare, two bedroom, pet friendly properties (pet fee required) will be sure to please you, your family, and friends. The main level enjoys a kitchen readily equipped with breakfast counter two stools. The living room features a wood-burning fireplace, queen sofa sleeper, love seat and recliner, 46”... View all property information
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    1 / 15
    Killington
    1 Bedroom / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Gym
    • Shared Outdoor Pool...
    • Wi-Fi
    • Hot Tub
    • Sauna
    • Fireplace
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Second floor property, up one flight of stairs from the parking lot and directly across from the sports center. The main level is an open floor plan. The kitchen is equipped with a refrigerator, stove, microwave, dishwasher, toaster, coffee pot, breakfast counter with four stools, and a... View all property information
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    1 / 3
    Killington
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Dishwasher
    • Sauna
    • Fireplace
    • Internet Access
    • Linens Provided
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This Unit has been rented for the full winter season!!! Bright, clean, and well-maintained, this unit will have you coming back year after year. The main level features the kitchen fully equipped with a refrigerator, stove, microwave, dishwasher, toaster, coffee pot, blender, breakfast counter with... View all property information
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