Hot Chester Cottage Rates

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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
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 ...
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
With a stay at this cottage, you'll be centrally located in Winhall, within a 5-minute drive of Bromley Mountain Ski Resort and Green Mountain National ...
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
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.
Opens in a new windowRenovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
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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
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 ...
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 AU$763 per night from 12 Nov to 13 Nov
AU$763
12 Nov - 13 Nov
includes taxes & fees
Located in Cavendish, Terrific 3-bedroom cottage with AC in charming Cavendish is in the mountains, within a 15-minute drive of Phineas Gage Memorial and Stoughton ...
Opens in a new windowTerrific 3-bedroom cottage with AC in charming Cavendish
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 ...
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
With a stay at this cottage in Chester, you'll be within a 15-minute drive of Springfield Art and Historical Society Museum and Springfield Nature Area.
Opens in a new windowPeaceful Brookside Getaway ~10 Mi to Okemo Slopes!
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, within a 15-minute drive of Bromley Mountain Ski Resort and West River.
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
When you stay at this cottage in Reading, you'll be on a river and 11 minutes by car from Mt Ascutney State Park.
Opens in a new windowCozy cottage on the river, minutes from skiing, horse events, and so much more!
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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$327
Highest Price
AU$763
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 AU$621 per night from 30 Nov to 1 Dec
AU$621
30 Nov - 1 Dec
includes taxes & fees
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 ...
Opens in a new windowWoodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
Opens in a new windowThe Shire Woodstock
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
The price is AU$389 per night from 23 Nov to 24 Nov
AU$389
23 Nov - 24 Nov
includes taxes & fees
With a stay at Jackson Gore Village in Ludlow (Jackson Gore Base Area), you'll be within a 15-minute walk of Okemo Mountain Resort and Jackson Gore Parking.
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 AU$327 per night from 1 Dec to 2 Dec
AU$327
1 Dec - 2 Dec
includes taxes & fees
With a stay at Kimpton Taconic Hotel by IHG in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and 5 minutes ...
Opens in a new windowKimpton Taconic Hotel by IHG
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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.