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$3,314 total

includes taxes & fees

1 Nov - 2 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$7,903 total

includes taxes & fees

21 Oct - 22 Oct

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

Andover

Lorraine C.

HK$5,555 total

includes taxes & fees

21 Oct - 22 Oct

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

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

Ludlow

HK$3,476 total

includes taxes & fees

3 Nov - 4 Nov

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

21 Oct - 22 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

21 Oct - 22 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$4,475 total

includes taxes & fees

21 Oct - 22 Oct

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$6,536 total

includes taxes & fees

21 Oct - 22 Oct

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

The Jackson

10/10 Excellent

"Quaint and elegant property. Thebinsite restaurant was great. Enjoyed our 1 night stay here at The Jackson."

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!"

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."

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