Chester Vacation Homes

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Our top choices for Chester holiday homes

1. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

HK$3,340 total

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a deck, surrounded by dense forest.

2. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

HK$7,850 total

includes taxes & fees

22 Oct - 23 Oct

3. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

Lorraine C.

HK$5,520 total

includes taxes & fees

22 Oct - 23 Oct

A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

4. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Ludlow

HK$3,562 total

includes taxes & fees

26 Oct - 27 Oct

A cozy living room with a fireplace, comfortable seating, and a television.

5. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Ludlow

HK$3,162 total

includes taxes & fees

22 Oct - 23 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

6. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

Tina l.

HK$3,936 total

includes taxes & fees

18 Nov - 19 Nov

A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

7. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly

Cheri V.

HK$3,867 total

includes taxes & fees

22 Oct - 23 Oct

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

8. Lakefront Family Fun Retreat

Newport

sean c.

HK$3,244 total

includes taxes & fees

3 Nov - 4 Nov

A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

9. Cozy Vermont Tiny Home Get Away

Brattleboro

HK$816 total

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton

HK$2,010 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

11. New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow

Tara

HK$4,693 total

includes taxes & fees

22 Oct - 23 Oct

A two-story house with a covered porch and a garage.

12. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Mount Holly

Chi L.

HK$6,536 total

includes taxes & fees

22 Oct - 23 Oct

A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

13. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Londonderry

"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "

Christine M.

HK$3,944 total

includes taxes & fees

27 Oct - 28 Oct

A garden with a wooden pergola, purple flowers, and a river view.

14. Family Friendly Hilltop House In Putney Vermont

Putney

Susan G.

HK$2,051 total

includes taxes & fees

26 Oct - 27 Oct

A compact kitchen with a refrigerator, stove, microwave, and sink.

15. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

Plymouth

HK$4,445 total

includes taxes & fees

21 Oct - 22 Oct

A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

16. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Jamaica

Luke B.

HK$4,790 total

includes taxes & fees

3 Nov - 4 Nov

A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

17. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Londonderry

Tim M.

HK$9,607 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living area with a fireplace, a dining area, and a kitchen.

18. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Ludlow

"My family and I stayed at this property last weekend and it was amazing!!! We were the first to rent as this is a brand new construction home. Everything inside is brand new from the bedding, furniture and amazing cookware. This house has a few great features that make it top notch: 1: Every bedroom has an en-suite bathroom, so we all had our own space and privacy. The bedrooms were big and beds were so comfortable. The master bedroom has this huge shower and tub that was so nicely designed. 2:...

Michael

HK$17,718 total

includes taxes & fees

21 Oct - 22 Oct

A living room with a brick fireplace, a sofa, a chair, and a coffee table.

19. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall

Mark H.

HK$6,589 total

includes taxes & fees

1 Nov - 2 Nov

A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

20. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall

Victoria L.

HK$5,203 total

includes taxes & fees

21 Oct - 22 Oct

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Top Chester Hotel Reviews

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My husband and I went for weekend trip. Our stay couldn’t be more wonderful. The front desk was helpful. The rooms had toiletries and were clean. We didn’t expect a refrigerator in room, but was in room. Since off season, the garage parking was vey convenient and ample."

Hideaway Inn Mt. Snow

8/10 Good

"It was a tablet check in which was fairly easy but sends the room number and access code to your e mail address . The rooms were clean and tidy. Free hot drinks in an area on a lower floor. Check out didn’t work on the tablet, so used the telephone. Nobody answered that call, but a member of staff appeared and said everything was fine and we could leave. Diving distance to local restaurants and there were numerous. The gondola was close by, although we didn’t go to the top because it was raining hard and didn’t think we would see much."

Woodstock Inn & Resort

8/10 Good

"Enjoyed staying at the Woodstock Inn. Great location, anything you want to see in the town of Woodstock, plus a number of great hiking trails, are walking distance. The in hotel restaurants, Red Rooster and Richardson's Tavern, are outstanding. No charge valet or easy self-parking available. The lobby is a great place to hang out, it has a great oversized fireplace and afternoons between 400 - 500 coffee and tea are available in the lobby for guests. By the entrance to the Red Rooster, there is also a basket of locally grown apples available anytime. There is a game room off the lobby, which is also a great place to go. The guest room was really comfortable, especially the mattress. So why a four star rating and not five? The in room thermostats are restricted so that a guest cannot set the fan to continuous run. This is to be expected at a lower end Marriott, but not a hotel at this price point. If you like white noise while sleeping, or don't like the HVAC cycling off and on, this is a problem. I did ask the front desk and got a response about environmental responsibility and energy conservation. For $1,300 a night plus a resort fee, a guest should be able to run the HVAC whenever they want. The lobby furniture cushions are worn and the cushions sink at a level I would compare them to college dormitory furniture. A lot of day trippers who aren't hotel guests come into the lobby, which greatly contributes to the wear. Still a great place to stay."

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