Hot Windsor Cottage Rates

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Featured Cottages in Windsor

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
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
When you stay at this cottage in Woodstock, you'll be on the waterfront, within a 5-minute drive of Taftsville Covered Bridge and Green Mountain Rock Climbing ...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
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Brook Road Cabin

Brook Road Cabin

3.5 out of 5
1217 Brook Road, Goshen, NH
The price is AU$458 per night from 30 Apr to 1 May
AU$458
includes taxes & fees
30 Apr - 1 May
Located in Goshen, this cottage is within a 15-minute drive of Newport Golf Club and Newport Historical Society.
Brook Road Cabin
Historic Hanover Area Home, 16 Miles to Dartmouth!

Historic Hanover Area Home, 16 Miles to Dartmouth!

3 out of 5
Enfield
Located in Enfield, this cottage is within a 15-minute drive of Henry Laramie Wildlife Management Area and Canaan Town Library.
Historic Hanover Area Home, 16 Miles to Dartmouth!
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
Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee

Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee

Sunapee
Located in Sunapee, this cottage is a 3-minute drive from Lake Sunapee and 7 minutes from Wendell Marsh Wildlife Management Area.
Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee
Cozy Historic Hilltop Cottage with Mount Ascutney View

Cozy Historic Hilltop Cottage with Mount Ascutney View

Windsor
With a stay at this cottage in Windsor, you'll be within a 15-minute drive of Mt Ascutney State Park and Brownsville Trail.
Cozy Historic Hilltop Cottage with Mount Ascutney View
The Cairn,  1840s Cozy Stone Cottage, Pet Friendly

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Chester
Located in Chester, this cottage is within a 15-minute drive of Vermont Country Store and DaVallia Art & Accents.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
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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.

Windsor 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 Windsor 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 Windsor 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 Windsor, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Windsor Cottages essential information

Accommodation
76 Cottages
Lowest Price
AU$189
Highest Price
AU$583
Popular accommodation
Cozy Crescent Cottage, Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit, Cozy 1850s home on the riverfront with mountain & river views - dog-friendly, Brook Road Cabin, Historic Hanover Area Home, 16 Miles to Dartmouth!, Woodstock Village Carriage House, Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee, Cozy Historic Hilltop Cottage with Mount Ascutney View, The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Top trending hotels in Windsor

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd, Windsor, VT
The price is AU$342 per night from 30 Apr to 1 May
AU$342
includes taxes & fees
30 Apr - 1 May
When you stay at Fat Sheep Farm & Cabins in Windsor, you'll be 13 minutes by car from Hartland Public Library.
Fat Sheep Farm & Cabins
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 4 May to 5 May
AU$210
includes taxes & fees
4 May - 5 May
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 12 May to 13 May
AU$189
includes taxes & fees
12 May - 13 May
With a stay at Align Inn Vermont in Quechee, you'll be in a state park, within a 15-minute drive of Dartmouth College and Quechee Gorge Village.
Align Inn Vermont
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Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$583 per night from 26 May to 27 May
AU$583
includes taxes & fees
26 May - 27 May
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
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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.