Chester Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Chester holiday rentals

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

23 Oct - 24 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

26 Oct - 27 Oct

A red house with a covered porch and a chimney.

4. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

HK$2,865 total

includes taxes & fees

22 Oct - 23 Oct

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

5. Long Trail House at Stratton Mountain Resort

Stratton

Michael

HK$3,463 total

includes taxes & fees

25 Oct - 26 Oct

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

6. Fat Sheep Farm & Cabins

Windsor

Jessica

HK$1,391 total

includes taxes & fees

3 Nov - 4 Nov

A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

7. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Cavendish

Ania H.

HK$4,245 total

includes taxes & fees

23 Oct - 24 Oct

A two-story house with a porch, a staircase, and a front door.

8. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Ludlow

Mikhail R.

HK$1,873 total

includes taxes & fees

23 Oct - 24 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."

Find out more about Chester

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Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to DaVallia Art & Accents, or you can select a more secluded option if you're looking for a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffee shops and restaurants.

What are some of the best holiday rentals that Chester has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Chester?

Choose from 31 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of the family-friendly sights. Vermont Country Store and Lowell Lake State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals feature extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.

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Check prices for these dates

Our top choices for Chester holiday rentals

1. Charming Chester Farmhouse near Near VT Slopes

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

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

4. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

5. Long Trail House at Stratton Mountain Resort

6. Fat Sheep Farm & Cabins

7. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

8. Cozy Studio Condo with Great Location, WiFi & Kitchenette

9. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

10. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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

12. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

13. Efficient condo near slopes with kitchenette & great location

14. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

15. New Ludlow Village Home with Stunning Okemo Mountain View

16. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

17. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

18. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

19. Cozy cabin in charming Londonderry

20. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Find holiday rentals that suit your style

Top Chester Hotel Reviews

The Jackson

Pointe at Castle Hill Resort

Grand Summit Resort, A Vail Resorts Property

Hampton Inn and Suites Manchester

Colonial Motel

Hideaway Inn Mt. Snow

The Black Bear Lodge at Stratton Mountain Resort

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Fullerton Inn

Find out more about Chester

Frequently asked questions

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