Hot Chester Cottage Rates

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

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 patios. Popular attractions Bromley Mountain Ski Resort and Bromley Alpine Slide are located ...
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS

CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS

2 out of 5
Weston
Stay at this cottage in Weston. Enjoy air conditioning. Popular attractions Viking Nordic Center and West River are located nearby.
CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS
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 an in-room coffeemaker and air conditioning. Popular attractions The Art of Humor Gallery and Lake Raponda are located ...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Save an average of 15% on thousands of hotels when you're signed in
Vermont Country Cottage (Near Village)

Vermont Country Cottage (Near Village)

Londonderry
Stay at this cottage in Londonderry. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions West River and West River Farmers Market ...
Vermont Country Cottage (Near Village)
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

Dorset
Stay at this cottage in Dorset. Enjoy free WiFi, a garden, and patios. Popular attractions Dorset Playhouse and Merck Forest Farmland Center are located ...
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Cozy Crescent Cottage

Cozy Crescent Cottage

Lempster
Stay at this cottage in Newport. Enjoy free WiFi, a garden, and balconies. Popular attraction Crescent Lake is located nearby.
Cozy Crescent Cottage
Charming Cavendish Cottage: All-Season Retreat!

Charming Cavendish Cottage: All-Season Retreat!

2 out of 5
Cavendish
Stay at this cottage in Cavendish. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Phineas Gage Memorial ...
Charming Cavendish Cottage: All-Season Retreat!
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Woodstock
Stay at this cottage in Woodstock. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Taftsville Covered Bridge and Green Mountain Rock ...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
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 patios. Popular attractions Okemo Mountain Resort and Lake Rescue are located nearby.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
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.

Top trending hotels in Chester

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11, Chester, VT
Fully refundableReserve now, pay when you stay
The price is NZ$432 per night from 7 Jan to 8 Jan
NZ$432
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 3-star B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Stone Hearth Inn and Eatery
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$777 per night from 7 Jan to 8 Jan
NZ$777
includes taxes & fees
7 Jan - 8 Jan 2025
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Woodstock Inn & Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is NZ$263 per night from 5 Jan to 6 Jan
NZ$263
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
Hampton Inn and Suites Manchester
Save an average of 15% on thousands of hotels when you're signed in
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is NZ$341 per night from 5 Jan to 6 Jan
NZ$341
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 3.5-star spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Pointe at Castle Hill Resort
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.