Holiday Rentals in Chester

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Holiday Rentals in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (49)
"Private and great location. Communication was amazing. For the price it felt like an absolute steal. Will definitely be going back in the winter for a ski trip. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

10.0 out of 10, Exceptional, (1)
"My family and I had the most wonderful stay at this beautiful Townshend, VT home! It was not only spotless and cozy, but also perfectly pet-friendly—Julie truly thought of everything. Both our family’s and our pet’s needs were taken care of, which made the experience even more special.Julie’s communication and care were outstanding, and every detail in the home showed thoughtfulness. We felt completely at home and can’t wait to return. Highly recommend this property for anyone looking for a...
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very good, (41)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is €365
includes taxes & fees
5 Oct - 6 Oct
Long Trail House at Stratton Mountain Resort

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.4 out of 10, Very good, (58)
"Great location and super cute"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (30)
"Beautiful Area. "
Solitude Village at Okemo

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (8)
"This place is beautiful! It had everything we needed. The hosts were very communicative and encouraged us to contact them if we had any questions. We stayed at the treehouse to celebrate our 30th anniversary and it exceeded our expectations. I would highly recommend this cozy and quiet retreat."
The price is €294
includes taxes & fees
29 Oct - 30 Oct
Owl's Nest Treehouse

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (24)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is €550
includes taxes & fees
20 Oct - 21 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (176)
"We had a nice time, thank you. Enjoyed jacuzzi, fire outside and local pizza and waterfalls:) "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (28)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging

Winterplace at Okemo

4.0 star property
8.8 out of 10, Excellent, (24)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
Winterplace at Okemo

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

9.8 out of 10, Exceptional, (6)
"We had a wonderful stay."
The price is €495
includes taxes & fees
13 Oct - 14 Oct
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (235)
"Extremely cozy. Would highly recommend staying here."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (163)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
The price is €323
includes taxes & fees
14 Oct - 15 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.4 out of 10, Very good, (25)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
The price is €246
includes taxes & fees
6 Oct - 7 Oct
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

9.8 out of 10, Exceptional, (126)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

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

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
The price is €222
includes taxes & fees
5 Oct - 6 Oct
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (142)
"Cute cabin close to Okemo and town! Really enjoyed our stay and would definitely return. "
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (7)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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

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, apart-hotels, 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 favorite 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 depends 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 €222 per night. Entering your travel dates in the search wizard you might find 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 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?

Okemo Mountain Lodging: This holiday home rental outside of Chester is in the mountains, and equipped with daily housekeeping and an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals will I find in Chester?

Choose from 33 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 Museum of Mining and Minerals 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.