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Looking for Chester hotels? View all hotels in the Chester area.

We have over 400 properties in the Chester, Vermont area.
Please browse our top 30 properties below

Vacation Rentals in the Chester/West Dover area. (22 miles away)

	Awesome ski chalet in West Dover near Mt Snow #1280
	6 Beds	3 Baths	Sleeps 18	House
This an awesome, classic, six bedroom, three bathroom, ski chalet just three miles to Mount Snow. This West Dover home includes an indoor hot tub room with lounge chairs, sauna, pool table, two living rooms with big screen TVs, DVD movies, granite island kitchen, and a large marble ski room. If you like ...

Vacation Rentals in the Chester/Killington area. (26 miles away)

	Bright & Sunny farmhouse in Plymouth #637				From $350/night, $1,400/week
	10 Beds	3 Baths	Sleeps 27	House
Located down a country road, this renovated attached Vermont farmhouse is open, bright & sunny. The kitchen and kitchenette are both fully equipped with microwave, coffee maker, toaster and all necessary cooking and eating utensils. The large cozy combination dining room & living room feature ...


	Classic Vermont home located in Killington #636				From $495/night, $1,980/week
	8 Beds	3 Baths	Sleeps 24	House
This two level very spacious house is conveniently located to the Killington area. This house has been newly renovated with plenty of country farmhouse charm. Renovations include: new beds, spreads, drapes, deck, re-insulated attic and new foundation. The fully equiped kitchen has an extra large ...


	Three story chalet located 2 miles from ski lift #635				From $495/night, $1,980/week
	6 Beds	3 Baths	Sleeps 24	House
This three story chalet is located 2 miles from the Sky Ship lift. This comfortable, clean and friendly chalet is ideal for small or large groups. There is radiant heat in every bathroom. It is easily accessible with plenty of parking.


	Charming southern Vermont home near great skiing! #631				From $451/night, $1,804/week
	4 Beds	4 Baths	Sleeps 17	House
This is a charming and unique yellow "A" Frame home located off from the Killington Access Road and is walking distance to night clubs, restaurants, ski shops, and the shuttle bus stop. The home has all new carpeting, a brand new large front deck w/ patio furniture & gas grill, large & ...


	Clean comfortable contemporary home - Killington #630				From $500/night, $2,000/week
	4 Beds	3 Baths	Sleeps 14	House
This 3 level, clean comfortable contemporary home, is perfect for families, groups or couples. Fully equiped kitchen comes with an eating bar, the dining area seats 12, and the living room has a fireplace.


	East Killington home very luxurious #629				From $795/night, $3,180/week
	4 Beds	3 Baths	Sleeps 12	House
This New Luxurious 3 Level home (sleeps 12) sits on the Home Stretch Trail. KE3 is a tastefully built and decorated home w/wood, slate & carpeted floors, high ceilings, plenty of closet space, & lots of bright windows. Relax in the outdoor hot tub & watch the skiers go by! There is a magnificent ...


	Cozy 4 bedroom home great for skiers - Killington #628				From $745/night, $2,980/week
	4 Beds	3 Baths	Sleeps 12	House
This cozy three level home features an open floor plan with cathedral ceiling living room with fire view wood stove, Stereo, Cable/Color TV, VCR and plenty of comfortable seating. The dining area features a beautiful wood floor. Large sunny room with HOT TUB. Large Sauna. Entry mud room for skies ...


	Home with game room and great views - Rutland area #627				From $495/night, $1,980/week
	4 Beds	4 Baths	Sleeps 12	House
This very spacious contemporary 3 level home is privately located just off Route 100N with fabulous mountain views. The kitchen is fully equipped including plenty of cupboard space. The large open living room/dining room area is comfortably furnished and has a stone fireplace, The family room is loaded ...


	Cozy southern Vermont home great for skiers! #625				From $248/night, $992/week
	4 Beds	2 Baths	Sleeps 12	House
This unique Killington Road home has over 2,400 sq. ft. of space, with e-e-easy level car access. There are three entertaining/living rooms. One has a built-in tile & wood two person whirlpool tub with wet bar. A 4 person sauna is just down the hall. Cozy up in the other two living areas with ...


	Log cabin only 2.5 miles from Killington ski area! #624				From $248/night, $992/week
	4 Beds	2 Baths	Sleeps 12	Cabin
This log cabin is 2.5 miles from Killington ski area and 1 mile to the restaurants and night clubs. It has a new outside hot tub on the deck and a stone fireplace in the great room. There is an apartment on the lower level, which has their own entrance and does not have access to the hot tub.


	Beautiful Southern Vermont home #623				From $545/night, $2,180/week
	4 Beds	3 Baths	Sleeps 10	House
This contemporary 3 level home is privately located just off Route 100N. The tiled modern kitchen is fully equipped with a JennAir like stove & plenty of cupboard space. The dining room features a very large table set in front of a cushioned bay window seat. Comfortably furnished, the living room ...


	Secluded Killington Valley home #622				From $260/night, $1,040/week
	3 Beds	3 Baths	Sleeps 8	House
This secluded 3 bedroom 3 bath home may be surrounded by woods, but with its many windows is very bright. The entryway/mudroom has a slate floor with a large closet. The living room features a stone wood-burning fireplace. The cathedral ceiling sets off the attractive sitting area uniquely decorated ...


	Large 3 bedroom home in Pittsfield #621				From $170/night, $680/week
	3 Beds	2 Baths	Sleeps 10	House
This contemporary three level home is privately located just off Route 100N. The kitchen is fully equipped. The dining area has a large table that seats 6-8 people. The home features a foosball game, air hockey, and is also close to the VINS Snowmobile trail. (There is NO fireplace.)


	Single Family Ski Home in Killington #619				From $200/night, $800/week
	2 Beds	2 Baths	Sleeps 9	House
"Pete's Retreat" is located just off Route 4 close to Pico Mountain & Killington Mountain. This newly built home resides in a secluded area that is very accessible in any weather. The kitchen is fully equipped & furnished with lots of cupboard space and the dining area is open with ...


	Single family ski home near Shelburne Center #618				From $200/night, $800/week
	2 Beds	2 Baths	Sleeps 9	House
"Cooper's Place" is located just off Route 4 close to Pico Mountain & Killington Mountain. This newly built home resides in a secluded area that is very accessible in any weather. The kitchen is fully equipped & furnished with lots of cupboard space and the dining area is open with ...


	Spacious condo in Killington Village #617				From $249/night, $996/week
	4 Beds	2 Baths	Sleeps 1-10	Condo
Enjoy this economical, 2-level condo in the heart of Killington Village. Within walking distance to the Killington Golf Course in the summer and on the Killington shuttle route to the slopes in the winter. Nice view of the mountains. The unit has a gas fireplace and a deck. Layout of this condo is ...


	Attractive ski condo near Pico ski resort. #616				From $361/night, $1,444/week
	3 Beds	3.5 Baths	Sleeps 1-12	Condo
This is a very attractive large 3-level townhouse located between Killington & Pico Ski Resorts. Winterberry 4 is set back off Route 4 in Killington with only 3 other distinctive townhouses in a secluded, quiet & beautiful area. This particular unit is very tastefully decorated and well furnished. ...


	Cute southern Vermont condo near great skiing! #615				From $242/night, $1,954/week
	3 Beds	2 Baths	Sleeps 1-10	Condo
This condo features spacious, bright, cheerful and contemporary styling. Conveniently located off route 4, with an easy drive to Killington. Walking distance to a complete health club (extra charge), restaurant, shops, and ski repair. Living room features a cathedral ceiling and a marble fireplace. ...


	Vermont condo Ideal location for skiers #599				From $206/night, $824/week
	2 Beds	2 Baths	Sleeps 1-8	Condo
Within walking distance to the Killington Golf Course in the summer and on the Killington Shuttle route to the slopes in the winter. Enjoy this economical, 1 - level condo in the heart of Killington Village. Nice view of the mountains. The unit comes with a gas fireplace and a deck. Layout of this ...


	Conveniently located Killington Condo #598				From $206/night, $824/week
	3 Beds	2 Baths	Sleeps 1-8	Condo
You will surely enjoy this economical, 1-level condo in the heart of Killington Village. Within walking distance to the Killington Golf Course in the summer and on the Killington shuttle route to the slopes in the winter. Nice view of the mountains. The unit comes with a gas fireplace and a deck. ...


	The perfect Killington ski condo #593				From $325/night, $1,300/week
	2 Beds	2.5 Baths	Sleeps 10	Townhouse
This condo features spacious, cheerful and contemporary styling with two decks. Conveniently located off route 4, with an easy drive to Killington. Walking distance to a complete health club (extra charge), restaurant, shops, and ski repair. Ski on Ski off of "A Slope"


	Handsome Vermont Townhouse Rental #592				From $250/night, $1,000/week
	2 Beds	2 Baths	Sleeps 8	Townhouse
You will love this luxury townhouse development just located 2.5 miles from Killington’s main base lodge, Snowshed. It features a modern open kitchen, dining room and living room floor plan that is complimented with various antiques throughout. The kitchen is fully equipped. This unit also offers a ...


	Condo with nice view of mountains near Shelburne #591				From $187/night, $748/week
	2 Beds	2 Baths	Sleeps 8	Condo
Enjoy this economical, 1 - level condo in the heart of Killington Village. Within walking distance to the Killington Golf Course in the summer and on the Killington shuttle route to the slopes in the winter. Nice view of the mountains. The unit comes with a gas fireplace and a deck. Layout of this ...


	Cute condo in ski heaven - Killington #590				From $164/night, $656/week
	2 Beds	2 Baths	Sleeps 7	Condo
This unit was totally renovated over the summer of 2001. The condo offers a gas burning stone fireplace. The kitchen is fully furnished & equipped. There is a large deck outside with nice views, and it is only 3.5 miles to Snowshed, the main base lodge.


	Luxurious Southern VT townhouse near great skiing! #589				From $220/night, $880/week
	2 Beds	2 Baths	Sleeps 6	Townhouse
This luxury townhouse development is located 2.5 miles from Killington’s main base lodge, Snowshed. It features a modern open kitchen, dining room and living room floor plan that is complimented with various antiques throughout. The kitchen is fully equipped. This unit also offers a wood burning fireplace. ...


	Pretty Vermont condo with fifth floor view. #588				From $250/night, $1,000/week
	2 Beds	2 Baths	Sleeps 1-6	Condo
Located in Mountain Green's main building III, this unit faces the mountains/ski slopes and enjoys a fifth floor view. It is with in walking distance of the Killington Golf Course in the summer and has a private shuttle to the ski slopes in winter. The unit comes with a wood burning fireplace (wood ...


	Beautiful Condo w/ excellent view of Killington #587				From $250/night, $1,000/week
	2 Beds	2 Baths	Sleeps 1-6	Condo
Attractive condominium unit with excellent view of Killington. Take the shuttle to the lifts and ski back to the unit. After skiing enjoy the heated swimming pool in the recreation center next door to the unit.


	Condo w/ great views close to Shelburne Center #586				From $187/night, $748/week
	2 Beds	2 Baths	Sleeps 1-6	Condo
Enjoy the economical, 1 level condo, that has the space of a 3 bedroom unit, but is rented as a 2 bedroom unit. Overlooking the 16th fairway of the Killington Resort Golf course, this unit has nice views of the mountains and the valley below. Beautifully decorated by its meticulous owner, this unit ...


	Ski condo w/ mountain view near Rutland Vermont #585				From $187/night, $748/week
	2 Beds	2 Baths	Sleeps 1-6	Condo
Enjoy this economical, 1 - level condo in the heart of Killington Village. Within walking distance to the Killington Golf Course in the summer and on the Killington Shuttle route to the slopes in the winter. Nice view of the mountains. The unit comes with a gas fireplace and a deck. Layout of this ...

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Chester Vacation Rentals | Hotels