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Pittsfield Vacation Rentals

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  • Wonderful three bedroom two bathroom home located in the mountains of Pittsfield, Vermont - a postcard Vermont town. Hawk Landing is surrounded by lush woods, offering a perfect getaway for families and small groups. Only a short drive to all that Killington has to offer. This wonderful family home offers a European and Middle Eastern feel combined in a Vermont rustic chalet. Enjoy the wood burning fieldstone fireplace while lounging or dining in the open living and dining areas with Cathedral ceilings. During the summer months enjoy grilling on the large deck overlooking the beautiful back yard. Take advantage of the exclusive access to private swimming pond. Pittsfield borders the Green Mountain National Forest making for easy access to mountain biking, hiking and the VAST snowmobile trails.

    Don't forget your four legged family member is more than welcome to join you during your time away as this property is pet friendly (prior approval required).

    Main Level: Living Area with wood burning fireplace, 42" Flat screen TV with Satellite, Dining Area table seats 8, Fully equipped Kitchen with Electric cooking stove - 4 slice toaster - dishwasher - 12 cup coffee makers - Microwave
    2 bar stools.

    Large Deck off Dining area - grill, Bedroom - full bed with attached 1/2 bath.

    Lower Level: Bedroom - Full bed, Master Bedroom - Full bed with attached bathroom with oversized tub, 19" TV DVD player, Full bath, Washer/Dryer, Office room with Computer for use.

    Pittsfield
  • This home is set along the Tweed River just before the scenic Village of Pittsfield. Rustic, secluded with total privacy. Cell phone sercie is spotty and 4 wheel drive vehicles are required. Only a short 10 minutes drive to the Killington ski resort.

    The home is spacious and great for groups. When entering the house there is a ski /mud room, living room with a stone fireplace and cathedral ceilings. From here open the sliders to the deck and relax in your personal hot tub.

    It offers a comfortable kitchen with dining area. The main level of the house has 2 bedrooms and a full bath. Upper floor has a bedroom with a King sized bed and separate loft area with a futon and full bathroom. The lower level of the house offers a large family room with a ping pong table, foosball and dart board. The remaining 2 bedrooms each have 2 sets of bunk beds and share the 3rd bathroom. You will also find here the laundry area.

    Pittsfield
  • Glazebrook Townhome F3: Located near the top of the Killington access road, this 2 bedroom unit is one (1) mile to Ramshead and Snowshed Base lodges which is the drop off for the Killington children's programs. Just a little farther up the road you are at the Killington Peak base lodge.

    All of Glazebrook is within walking distance to restaurants and shops. Parking available immediately in front of the unit & no stairs or hallways to contend with. Just park & bring your gear in the first floor front door. Perfect for families with small children or those seeking convenience and comfort! You'll find Wi-Fi streaming throughout. The lower level consist of your entryway, large kitchen with breakfast bar, dining area and living room with wood burning fireplace a flat screen TV, as well as a half bath.

    Upstairs you will find 2 bedrooms. The Master bedroom with a queen size bed and a small deck. The bathroom has a Jacuzzi jetted tub and a dry sauna. There is also a washer & dryer in the upstairs hallway.

    This condo was great. Very clean and cozy.

    Killington 9.35 miles
  • Located near the top of the Killington access road, this 2 bedroom unit is one (1) mile to Ramshead and Snowshed Base lodges which is the drop off for the Killington children's programs. Just a little farther up the road you are at the Killington Peak base lodge.

    All of Glazebrook is within walking distance to restaurants and shops. Parking available immediately in front of the unit & no stairs or hallways to contend with. Just park & bring your gear in the first floor front door. Perfect for families with small children or those seeking convenience and comfort!

    You'll find Wi-Fi streaming throughout. The lower level consist of your entryway, large kitchen with breakfast bar, dining area and living room with wood burning fireplace a flat screen TV, as well as a shower bath.

    Upstairs you will find 2 bedrooms. The Master bedroom with a queen size bed and a small deck. The bathroom has a Jacuzzi jetted tub and a dry sauna. There is also a washer & dryer in the upstairs hallway.

    Awesome condo close to everything. Would definitely stay again.

    Killington 9.32 miles
  • Located near the top of the Killington access road, this 3 bedroom end unit is one (1) mile to Ramshead and Snowshed Base lodges. The drop off for the Killington children's programs. Just a little further up the road and you are at the Killington Peak base lodge.

    All of Glazebrook is within walking distance to restaurants and shops. Parking available immediately in front of the unit & no stairs or hallways to contend with. Just park & bring your gear in the first floor front door. Perfect for families with small children or those seeking convenience and comfort! You'll find Wi-Fi streaming throughout.

    The lower level consist of your entryway, large kitchen with breakfast bar, dining area and living room with wood burning fireplace a 51 inch flat screen TV, as well as a half bath. Off the Living room is your master suite with a King size bed, another flat screen TV and master bath with both a shower stall and large oval Jacuzzi jetted tub.

    Upstairs you will find 2 bedrooms, one with 2 twin beds and the other with a queens size bed & a dry sauna, another bathroom and washer & dryer.

    Had a fantastic place to spend the weekend. This is our 3rd time spending the weekend at the same house. We love the house and the area.

    Killington 9.34 miles
  • Unique authentic mountain Log-Cabin facing the Green Mountain National Golf Course. If you're looking for that special place look no further. The circular driveway leads up to the "Killington Moose Log-Cabin" a special comfortable home that gives you the rustics and modern demands we expect in today's world.

    The Log Cabin features cathedral ceilings, Stone fireplace and a life size moose head above, flat screen TV and wifi. The open floor plan leads you to the modern country kitchen with stainless steel appliances breakfast counter and dining room with an antler light fixture and a full bathroom.

    The upper level has the master bedroom with an en-suite bath and TV. The lower level has a family room with fireplace and sleeper sofa. Two bedrooms one with a full size bed the other feature a set of bunk beds. They share the 3rd bathroom and there is a washer and dryer.

    The Cabin has a magnificent private deck facing the golf course and a build in Hot tub.

    it was exactly what we were looking for in Killington, a great rustic getaway! our family really in joyed sitting around the fire each night..

    Killington 5.28 miles
  • Completely Remodeled Five bedroom private home. Close to Killington Mountain. Five bedrooms with three full bathrooms along with two half baths. Three level home with two full kitchens. You won't be disappointed with this property.

    Main Level: Fully equipped kitchen, Dining Table seats 10, Living Area with Wood Burning Fireplace, Sitting Area with Queen Futon, 1/2 bath, Upper Bedroom - Two bunk bed sets - both with lower full bed, Full Bathroom with whirlpool tub, Washer/Dryer, Bedroom with two twin beds, Bedroom with Full bed, Full Bathroom, Lower Level, Fully equipped kitchen, Sitting Area with Wood Burning Fireplace, Full bath, Bedroom with Bunk bed set lower bunk Full size, Bedroom with Bunk bed set lower bunk Full size.

    Easy check in, big house with lots of room. couldn't ask for anything else except to stay longer.

    Killington 8.96 miles
  • This premium, distinctive and spacious 4-level, 4 bedroom townhouse is located between Killington and Pico ski areas. Upon entering this home you will be able to drop your skis and gear into a large walk-in closet in your mud room.

    The main floor features a living room with a wood burning fireplace and 26" flat screen TV with DVD player. There is also a formal dining area that seats 8 and a fully equipped kitchen with a breakfast bar plus a half bath.

    The upper level hosts the master bedroom, a full bath. Unwind in the king size bed with your own 32inch TV in front of the gas fireplace or slip into something more comfortable in your personal dressing room and relax on the deck.

    On the lower level you will find a lounge room with queen-size sofa/bed, 26inch TV/DVD; a bedroom with 2 twin beds; a third bedroom with 2 sets of bunks, and its own full bathroom. Also downstairs is another full bath, a laundry room with washer/dryer.

    The lowest level is a bedroom with a queen size bed and vanity. Each level has its own deck accessible from each of the bedrooms. The main level deck has a 6 person hot tub with mountain views. A perfect vacation home!

    Square Footage: 2000 Square Feet.

    The place was lovely and nice. For the price that we paid I wish the place was more up to date and the heating would be better. All the floor below the living room was freezing. Betty was great and would book from them again for future event but I would look for another place.

    Killington 7.4 miles
  • Ski in/ski out right from your 2 bedroom condo, the trail is just 50 yards from your front door. Pamper yourself in this 2 bedroom, 2 bath condo with onsite Spa.

    The condo features a fully equipped kitchen that extends to a small dining area and large, long living room with sliders to your private deck and mountain vistas. The living room has a wood-burning fireplace and a 40" Flatscreen TV. There are two bedrooms, an entryway/mud room to store your ski equipment and 2 full bathrooms. The master bedroom features a queen size and second bedroom has 2 bunk beds.

    Square Footage: 1000 Square Feet.

    Excellent location, very clean. Will stay there again.

    Killington 12.22 miles
  • This spacious five bedroom chalet located smack in the Center of the Killington Basin area. Just minutes away from Killington Road, Snowshed, Ramshead and Killington Base Lodges. In between you find all the ski shops, Restaurants, bars and night life Killington has to offer. Enter the large foyer and sit down to take off your gear. There are three bedrooms with two twin beds each and a bedroom with a queen size bed. As well as a full bath room. Upstairs you find the master bedroom with a King size bed and full bath.

    A bright and sunny Living room with a gas fireplace, Dining area and fully equipped Kitchen. Large windows and sliders open up to a deck up front. The master bedroom with King. The home makes an excellent choice for several families or a group of friends who want a comfortable ski home in close proximity to the slopes of Killington and the night life. Pets possible.

    Square Footage: 2000 Square Feet.

    House worked perfectly for our weekend getaway from the City. Our pup thoroughly enjoyed the fences in yard and the baby slept through the nights in the downstairs bedroom. Temp was a little hard to control as it got too hot when the heat was on and too cold when we lowered it, but overall, great house.

    Killington 8.33 miles
  • Winterberry 2 is a modern and contemporary townhouse, which is a very bright and spacious 3-level, 4 bedroom townhouse with WiFi throughout. Winterberry 2 has just been remodelled and is new to the rental market. This townhouse offers a very high standard of accommodation and great attention to detail with the customer in mind. It is located in a beautiful wooded area set within close proximity of both the Killington and Pico ski areas both of which are just a few moments drive away. Nearby activities include downhill skiing, cross-country skiing, snowshoeing, biking and hiking.

    Upon entering this home you leave your skis and gear the large closet in the mud room. The living room on this level is in a contemporary style with beautiful wood floors and a large stone surround open log burning fireplace. There is a wall mounted 50 inch flat screen Xfinity SMART TV and DVD player which can be viewed from both the living and dining areas. Sliding doors from the dining area lead to the private deck and your own 6 person hot tub with views of both Killington and Pico peaks where you can relax and watch the trails being groomed after a day on the slopes. The spacious dining area seats 10. There is a fully equipped kitchen with all new appliances that is a pleasure to cook in. There is also a half bath on this level.

    The upper level hosts the master suite consisting of a impressive bedroom with a king sized bed, sofa and Xfinity TV, a personal dressing room and a bathroom suite which includes a large Jacuzzi bath and bidet. Relax in front of the 32inch Xfinity flat screen TV or slip into something more comfortable and relax on the private deck. On the lower level you will find three further bedrooms. The second bedroom has a queen size bed with a 32inch Xfinity flat screen TV and an ensuite full bathroom with its own access to the deck. The third bedroom has 2 twin beds with its own access to a private deck. The fourth bedroom has 2 sets of bunks. Also on this level is a full family bathroom and a laundry room with washer/dryer.

    Square Footage: 2000 Square Feet.

    Great place. Everything perfect except kitchen could use pots, bowls, etc. Hard to make a dinner for 8 with items supplied. Overall would come back bringing what I know is missing.

    Killington 7.4 miles
  • Enjoy this upscale Four bedroom, three bathroom Private home with large wrap around deck. Families and Friends can enjoy the game room located on the bottom floor of the three story home! Pool table, ping-pong, air hockey and foosball tables. This spacious lodge can accommodate a maximum of 12 people. On the main floor, you will find a king and queen bedroom that share a bathroom with a whirlpool tub as well a second queen bedroom with a full bathroom. Upstairs in the 'kids' room, you will find two sets of bunk beds, tv, vcr and another full bathroom. Additional amenities include a queen sleeper sofa in the living room, a futon and private washer and dryer.

    Located in an appealing wooded property a 1/4 mile up the Killington Access road. Perfect private home for all families and your favorite traveling companions! This beautifully decorated lodge is perfect for Skiers, Snowboarders and those who love the beautiful fall foliage. You will also be within minutes to the Gifford Woods State Park, Killington and Pico Mountains.

    Sunset Lodge will give you all the cozy comforts for your trip to Killington. Plenty of comfortable living space sporting exposed beam ceilings, large windows to filter in light to brighten your days and showing off the surrounding wooded view. After your day of hitting the slopes you can keep toasty warm by the wood fireplace. Relax while watching your favorite shows on the large flat screen tv or bring your favorite movies using the DVD and VCR players. Enjoy streaming your favorite shows/movies, browsing the internet using the high speed wifi.

    A beautiful kitchen with granite counter tops, lots of cook ware to enjoy those home cooked meals with your family. To tired to cook? Dont worry you are minutes from the dinning Killington has to offer! Enjoy your mornings at the breakfast bar drinking your favorite cup of coffee or having your big breakfast in the adjacent room that seats eight. Don't worry about doing the dishes, take advantage of loading the dishwasher to clean up so you can head out for your daily activities!

    Whether you are in Killington during the warm summers or cooler colorful autumn days and nights, you can keep on making memories with your traveling companions! The wrap around deck features an outdoor grill or you can move inside to the private game room for friendly competitions of Ping-pong, pool, foosball and air hockey!

    The house was great, close to the mountain and restaurants. Game room in the basement was fun and the fireplace was excellent to relax next to. Beautiful place lots of space perfect for our group.

    Killington 7.53 miles
  • Beautiful Renovated Country home with restored pine floors, 5 bedrooms with flat screen TV's in each. Gorgeous fireplace with large flat screen TV.

    Main Level: Kitchen - fully equipped kitchen - gas cooking stove, Microwave, Dishwasher, All new stainless Steel Appliances, Living room with large wood burning fireplace, 55" flat screen TV with bluray, Bedroom - King bed with 32" flat screen TV with bluray, Full bath.

    Upper level: Bedroom - Full bed with 21" flat screen TV with DVD player, Bedroom - Queen bed with 21" flat screen TV, Bedroom - Two twins with 32" flat screen TV, Bedroom - King with 32" flat screen TV, Full bathroom.

    Lower Level: Laundry room with washer/dryer, Family Room with 46" TV, Two sets of bunk beds - each bed on each bunk has a full bed - top bunk twin beds, Queen Sleeper Sofa, Full bathroom, Video Game room with 6 video games.

    Enjoy the 8 person outdoor hot tub!! This property is for the "family" atmosphere at all times. We rent to families and responsible adults ONLY. If you are looking for a party house, please do not choose this property.

    The hot tub worked!!!

    Killington 4.21 miles
  • Winterberry 4 is a premium, distinctive, spacious and sunny 4-level, 4 bedroom townhouse with WiFi throughout.

    This home offers a very high standard of accommodation and is located in a beautiful area set within close proximity of both the Killington and Pico ski areas both of which are only a few moments drive away. Nearby activities include downhill skiing, cross-country skiing, snowshoeing, biking and hiking.

    Upon entering you will be able to drop your skis and gear into a large walk-in closet in your mud room. You will be greeted on the main floor by amazing views from the floor to ceiling sliding windows in both the living and dining areas.

    The living room on this level has been recently updated in a contemporary style with beautiful wood floors and a large stone surround open log burning fireplace. It has a wall mounted 40 inch flat screen Xfinity TV and DVD player. Sliding doors lead to the private deck and your own 6 person hot tub with views of both Killington and Pico peaks where you can relax and watch the trails being groomed after a day on the slopes. There is a welcoming dining area that seats 10, a large recently fitted fully equipped kitchen that is a pleasure to cook in and includes a breakfast bar. There is also a half bath on this level.

    The upper level hosts the master bedroom with a queen sized bed, the ensuite bathroom includes a whirlpool tub and a shower. Unwind in the queen size bed with your own wall mounted 32inch Xfinity flat screen TV or slip into something more comfortable in your personal dressing room and relax on the private deck.

    On the lower level you will find a lounge room with queen-size sofa and 32 inch flat screen Xfinity TV. The second bedroom has 2 twin beds with its own access to a private deck. The third bedroom has 2 sets of bunks with an ensuite bathroom and access to the deck.
    Also on this level is a family bathroom and a laundry room with washer/dryer.

    On the lowest level you will find the forth bedroom with a queen size bed and 32inch flat screen Xfinity TV.

    Square Footage: 2000 Square Feet.

    Very well done. Check in and out was very good. Instructions for checkout were great. Beds, linens, cutlery, hot tub, tv, all worked. Hot and cold water plus good parking space available was a plus. Place overall was very nice. Met and exceeded expectations for its price.

    Killington 7.4 miles
  • Large 6 bedroom 4 bath home with private hot tub in the heart of Killington. Just finished a 6 week renovation. New cherry kitchen with granite counter tops, stainless steel appliances. Large living room with cathedral ceilings. Living room features a 55" smart TV and a wood burning fireplace. Huge family room. 4 bedrooms feature queen beds and there is a bedroom with 2 sets of bunk beds and a bedroom with another bunk. The house has 3 levels and over 3000 square feet of space. It has ample off street parking. For summer renters there is a large deck and large yard for outdoor enjoyment. All in all a perfect vacation home.

    Square Footage: 3000 Square Feet.

    This was our annual ski trip. The house was very close to the slopes. The great room was perfect! The fireplace was key!!! The kitchen was our central hub. We all loved the hot tub. Prior to coming I did call to inquire if there was a grill and was told there was not. When I pulled up - there was a grill. Wish that was listed. We were allowed to check in early which was a great perk!

    Killington 9.14 miles

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