Chester Vacation Rentals from $157: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Chester?

Mountainside 5-BR Ski-In/Out Okemo Villa : Located near Chester, this vacation home rental is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 hot tub.

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Our top choices for Chester vacation rentals

Brand New Luxury “Tiny” House, Immersed In Nature

Athens

Mia G.

$398 nightly

May 12 - May 13

Total with taxes and fees

LUXE Forest Retreat

Chester

$430 nightly

May 12 - May 13

Total with taxes and fees

Cozy Vermont Cabin · Mountain Views · Near Okemo

Chester

pauline

$970 nightly

Jun 1 - Jun 2

Total with taxes and fees

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Andover

$511 nightly

May 12 - May 13

Total with taxes and fees

Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Stephanie F.

$365 nightly

May 21 - May 22

Total with taxes and fees

Long Trail House at Stratton Mountain Resort

Stratton

William

$346 nightly

Jun 2 - Jun 3

Total with taxes and fees

Owl's Nest Treehouse

Alstead

Garrett B.

$313 nightly

May 17 - May 18

Total with taxes and fees

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Jake D.

$322 nightly

May 14 - May 15

Total with taxes and fees

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Top Chester Hotel Reviews

Best Western Plus Keene Hotel

6/10 Okay

"Great people, location, but just needs some renovatetions and our room smelled. It has a great bar but it closed at 9pm - that,s like prime time for drinks after dinner and sport events on TV etc --what good is that ? Still decent.place to stay. . "

Fullerton Inn

10/10 Excellent

"Fun stay at a neat old inn in a very convenient and lovely location, walking distance to good food and shopping. This is an older hotel that doesn’t have all the updated and most modern conveniences but if it did, it would be twice as expensive and I probably would not have stayed there. And it would probably lose some of its charm. Lovely on site restaurant and every thing is very clean and neat, freshly painted, I would, and probably will, stay here again next time I am in the area. Very comfortable place to stay. The staff is very friendly and helpful."

The Palmer House Resort, an Ascend Collection Hotel

2/10 Terrible

"I am a family travel blogger who stays in hotels frequently with my husband and two young daughters. This was the most disappointing hotel experience we have had. We booked this stay for Mother’s Day weekend and arrived expecting a comfortable, family-friendly experience. From the moment we arrived, the property appeared noticeably run-down compared to what was advertised online. When we entered the lobby, there was a sign at the front desk stating, “Helping another customer. Be right back.” We waited approximately 15 minutes with no staff member present before leaving to take our children elsewhere and returning later. Upon returning, the front desk informed us that although I had reserved a king room with a sleeper sofa, the reservation had been entered for only two guests. I explained that we were traveling with our young kids and expected the sleeper sofa to accommodate them. Rather than offering flexibility or assistance, we were told the only option was to purchase an additional adjoining room. What made this especially frustrating was that the hotel appeared nearly empty, with very few cars in the parking lot and clearly many available rooms. As a traveling family arriving on Mother’s Day weekend, the interaction felt unnecessarily rigid and financially motivated rather than customer-focused or accommodating. We no longer felt comfortable staying at the property and chose instead to leave. Because the reservation was made through Hotels.com we were not given a refund."

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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?

Mountainside 5-BR Ski-In/Out Okemo Villa: Located near Chester, this vacation home rental is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 hot tub.

How many vacation rentals will I find in Chester?

Choose from 32 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 The Nature Museum 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.

Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Brand New Luxury “Tiny” House, Immersed In Nature

LUXE Forest Retreat

Cozy Vermont Cabin · Mountain Views · Near Okemo

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Charming Chester Farmhouse near Near VT Slopes

Long Trail House at Stratton Mountain Resort

Owl's Nest Treehouse

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Outdoor Adventure Hub! Family Home in West Dover

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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

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

Lake Front Family Friendly Escape

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Family Friendly Hilltop House In Putney Vermont

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

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Best Western Plus Keene Hotel

Find out more about Chester

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