Hot Chester Cottage Rates

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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}
Cozy Crescent Cottage

Cozy Crescent Cottage

Lempster
Book a stay at this family-friendly cottage in Newport. Enjoy free WiFi, a garden, and balconies. Popular attractions Crescent Lake and Gallop Marsh State Wildlife ...
Cozy Crescent Cottage
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
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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 Dorset Village Public Library are located ...
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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

Walpole
The price is NZ$432 per night from 6 Apr to 7 Apr
NZ$432
includes taxes & fees
6 Apr - 7 Apr
Stay at this cottage in Walpole. Enjoy 2 outdoor pickleball courts, an in-room coffeemaker, and air conditioning. Popular attractions Hooper Golf Course and ...
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Unique Ski cottage nestled between Mt. Snow & Stratton

Unique Ski cottage nestled between Mt. Snow & Stratton

Wardsboro
Stay at this cottage in Wardsboro. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Wardsboro Public Library and Margie's Muse Handweaving ...
Unique Ski cottage nestled between Mt. Snow & Stratton
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
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock
Stay at this cottage in Woodstock. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Dana House Museum and Billings Farm and Museum ...
Woodstock Village Carriage House
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)
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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$243
Highest Price
NZ$644
Popular accommodation
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}, Cozy Crescent Cottage, Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit, Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!, Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro, Unique Ski cottage nestled between Mt. Snow & Stratton, Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Woodstock Village Carriage House, Vermont Country Cottage (Near Village)

Top trending hotels in Chester

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
The price is NZ$243 per night from 16 Apr to 17 Apr
NZ$243
includes taxes & fees
16 Apr - 17 Apr
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$644 per night from 6 Apr to 7 Apr
NZ$644
includes taxes & fees
6 Apr - 7 Apr
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
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road, Brownsville, VT
Fully refundable
The price is NZ$247 per night from 6 Apr to 7 Apr
NZ$247
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our ...
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 8 Apr to 9 Apr
NZ$304
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
The Equinox Golf Resort & Spa
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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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^Subject to availability and chosen travel dates.