Chester Vacation Rentals from ￥28,092: Search Short-Term Rentals

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Our top choices for Chester vacation rentals

1. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

￥66,722 total

includes taxes & fees

Nov 2 - Nov 3

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

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

Chester

pauline

￥159,656 total

includes taxes & fees

Nov 1 - Nov 2

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

Andover

Lorraine C.

￥111,853 total

includes taxes & fees

Nov 1 - Nov 2

A red house with a covered porch and a chimney.

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

Grafton

Eleanor D.

￥57,696 total

includes taxes & fees

Oct 21 - Oct 22

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

￥69,730 total

includes taxes & fees

Oct 21 - Oct 22

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

6. Fat Sheep Farm & Cabins

Windsor

Jessica

￥28,092 total

includes taxes & fees

Nov 3 - Nov 4

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.

￥86,013 total

includes taxes & fees

Oct 28 - Oct 29

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.

￥37,714 total

includes taxes & fees

Oct 21 - Oct 22

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Top Chester Hotel Reviews

Pointe at Castle Hill Resort

8/10 Good

"The hotel was clean but older. Nothing special. Basic hotel room."

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."

Find out more about Chester

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Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals in Chester near DaVallia Art & Accents, or you can select a more remote option if you want 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 coffeehouses and restaurants.

What are some of the best vacation rentals in Chester?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Chester is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Chester?

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

What’s there to see and do in Chester?

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

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Chester vacation 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 vacation rentals that suit your style

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Grand Summit Resort, A Vail Resorts Property

Hampton Inn and Suites Manchester

Jackson Gore Village, A Vail Resorts Property

Colonial Motel

Hideaway Inn Mt. Snow

Woodstock Inn & Resort

Latchis Hotel

The Black Bear Lodge at Stratton Mountain Resort

Find out more about Chester

Frequently asked questions

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