Chester Holiday Rentals

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Holiday Rentals in Chester

Holiday Home in Chester Depot

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is AU$227
includes taxes & fees
20 Nov - 21 Nov
Whimsical Room & Private Bathroom in Historic Inn

Holiday Home in Chester Depot

9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is AU$541
includes taxes & fees
23 Nov - 24 Nov
Chester Farmhouse Ski Retreat near Slopes

Holiday Home in Chester

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is AU$1,547
includes taxes & fees
20 Nov - 21 Nov
Cozy Vermont Cabin · Mountain Views · Near Okemo

Apartment in Bridgewater

9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is AU$301
includes taxes & fees
1 Dec - 2 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking

Condo in Clock Tower Base Area

9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is AU$404
includes taxes & fees
23 Nov - 24 Nov
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Dover

8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is AU$451
includes taxes & fees
21 Nov - 22 Nov
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Clock Tower Base Area

9.2 out of 10, Wonderful, (25)
"Loved the location"
United States
Steven W.
The price is AU$380
includes taxes & fees
2 Dec - 3 Dec
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Holiday Home in Putney

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is AU$395
includes taxes & fees
23 Nov - 24 Nov
Family Friendly Hilltop House In Putney Vermont

Aparthotel in Stratton

3.0 star property
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is AU$595
includes taxes & fees
20 Nov - 21 Nov
Long Trail House at Stratton Mountain Resort

Condo in Ludlow

10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is AU$451
includes taxes & fees
20 Nov - 21 Nov
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Condo in Ludlow

9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is AU$363
includes taxes & fees
2 Dec - 3 Dec
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Cabin in Newfane

2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is AU$395
includes taxes & fees
1 Dec - 2 Dec
Wellness Getaway with a Personal Sauna, and Private River Beach!

Apartment in Bromley Mountain

9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
The price is AU$505
includes taxes & fees
20 Nov - 21 Nov
Cozy Bromley Retreat

Cabin in Cavendish

2.0 star property
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is AU$480
includes taxes & fees
20 Nov - 21 Nov
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Condo in Ludlow

8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is AU$363
includes taxes & fees
2 Dec - 3 Dec
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Holiday Home in Newport

10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is AU$578
includes taxes & fees
3 Dec - 4 Dec
Lake Front Family Friendly Escape

Condo in Ludlow

9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
The price is AU$404
includes taxes & fees
2 Dec - 3 Dec
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Apartment in Ludlow

8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is AU$318
includes taxes & fees
1 Dec - 2 Dec
Efficient condo near slopes with kitchenette & great location

Chalet in Plymouth

2.0 star property
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is AU$697
includes taxes & fees
23 Nov - 24 Nov
Pet-friendly winter retreat in the woods near Okemo + Killington

Apartment in Ludlow

8.8 out of 10, Excellent, (29)
"Great location and great place!"
United States
Linda G.
The price is AU$332
includes taxes & fees
1 Dec - 2 Dec
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$404 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Bonnie's Bundles Dolls, 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 34 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of the family-friendly sights. Stratton Mountain Resort and Vermont Country Store 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.