Hot Chester Cottage Rates

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Chester

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

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

Wilmington
Stay at this cottage in Wilmington. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions The Art of Humor Gallery and Lake Raponda ...
Opens in a new windowCottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

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

Winhall
Stay at this cottage in Winhall. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bromley Mountain Ski Resort and Bromley Alpine Slide ...
Opens in a new windowBeautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Ludlow
Stay at this cottage in Ludlow. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Lake Rescue are located ...
Opens in a new windowRenovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Save an average of 15% on thousands of hotels when you're signed in
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Dorset
Stay at this cottage in Dorset. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Dorset Playhouse and Dorset Village Public Library are ...
Opens in a new windowCharming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish

Cavendish
The price is NZ$873 per night from 6 Nov to 7 Nov
NZ$873
6 Nov - 7 Nov
includes taxes & fees
Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Stoughton Pond Recreation Area and Phineas Gage Memorial are located nearby.
Opens in a new windowTerrific 3-bedroom cottage with AC in charming Cavendish
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock
Stay at this cottage in Woodstock. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Dana House Museum and Billings Farm and Museum are ...
Opens in a new windowWoodstock Village Carriage House
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3 out of 5
Chester
Stay at this 3-star cottage in Chester. Enjoy free parking, an in-room coffeemaker, and in-room fireplaces. Popular attractions Springfield Art and Historical ...
Opens in a new windowPeaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Vermont Country Cottage (Near Village)

Vermont Country Cottage (Near Village)

Londonderry
Stay at this cottage in Londonderry. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions West River and West River Farmers Market ...
Opens in a new windowVermont Country Cottage (Near Village)
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Reading
Stay at this cottage in Reading. Enjoy free WiFi, laundry facilities, and patios. Popular attraction Mount Ascutney is located nearby.
Opens in a new windowCozy cottage on the river, minutes from skiing, horse events, and so much more!
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Chester Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Chester will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Chester definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Chester, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Chester Cottages essential information

Accommodation
152 Cottages
Lowest Price
NZ$378
Highest Price
NZ$873
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}, Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit, Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!, Terrific 3-bedroom cottage with AC in charming Cavendish, Woodstock Village Carriage House, Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!, Vermont Country Cottage (Near Village), Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Top trending hotels in Chester

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$700 per night from 30 Nov to 1 Dec
NZ$700
30 Nov - 1 Dec
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowWoodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowThe Shire Woodstock
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
The price is NZ$396 per night from 6 Nov to 7 Nov
NZ$396
6 Nov - 7 Nov
includes taxes & fees
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Opens in a new windowJackson Gore Village
Save an average of 15% on thousands of hotels when you're signed in
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is NZ$378 per night from 1 Dec to 2 Dec
NZ$378
1 Dec - 2 Dec
includes taxes & fees
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
Opens in a new windowKimpton Taconic Hotel by IHG
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.