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
A stay at this cottage places you in the heart of Winhall, steps from Green Mountain National Forest and a 5-minute drive from Bromley Mountain Ski Resort.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cozy Crescent Cottage

Cozy Crescent Cottage

Lempster
Located in Newport, this cottage is on the waterfront, a 1-minute drive from Crescent Lake and 7 minutes from Gallop Marsh State Wildlife Management Area.
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
With a stay at this cottage in Ludlow, you'll be on the beach, within a 10-minute drive of Okemo Mountain Resort and Lake Rescue.
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
With a stay at this cottage in Dorset, you'll be in the mountains, just a 1-minute walk from Green Mountain National Forest and 5 minutes by foot from Dorset ...
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 AU$400 per night from 6 Apr to 7 Apr
AU$400
includes taxes & fees
6 Apr - 7 Apr
Located in Walpole, this cottage is in a rural location, within a 10-minute drive of Connecticut River and Walpole Artisans Cooperative.
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
Located in Wardsboro, this cottage is in a rural location, within a 5-minute drive of Green Mountain National Forest and Wardsboro Public Library.
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
With a stay at this cottage in Wilmington, you'll be near the beach, just a 1-minute walk from Lake Raponda and 12 minutes by foot from The Art of Humor ...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock
With a stay at this cottage in Woodstock, you'll be on the waterfront, just a 1-minute walk from Marsh-Billings-Rockefeller National Historical Park and 6 minutes ...
Woodstock Village Carriage House
Vermont Country Cottage (Near Village)

Vermont Country Cottage (Near Village)

Londonderry
With a stay at this cottage in Londonderry, you'll be in the mountains, just a 1-minute walk from West River and 9 minutes by foot from West River Farmers ...
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
AU$222
Highest Price
AU$590
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 AU$222 per night from 5 Apr to 6 Apr
AU$222
includes taxes & fees
5 Apr - 6 Apr
Located in Chester (Chester Depot), Fullerton Inn is within a 15-minute drive of Vermont Country Store and Springfield Hospital.
Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$590 per night from 6 Apr to 7 Apr
AU$590
includes taxes & fees
6 Apr - 7 Apr
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
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 AU$227 per night from 7 Apr to 8 Apr
AU$227
includes taxes & fees
7 Apr - 8 Apr
Located in Brownsville, Holiday Inn Club Vacations Mount Ascutney Resort by IHG is in a national park, within a 15-minute drive of American Precision Museum ...
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 AU$279 per night from 6 Apr to 7 Apr
AU$279
includes taxes & fees
6 Apr - 7 Apr
When you a stay at The Equinox Golf Resort & Spa in Manchester, you'll be in the mountains, just steps from Green Mountain National Forest and Golf Club at ...
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.