Hot Windsor Cottage Rates

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Featured Cottages in Windsor

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse

Hartford VT
The price is AU$332 per night from 26 May to 27 May
AU$332
26 May - 27 May
includes taxes & fees
With a stay at this cottage in Wilder, you'll be within a 15-minute drive of Dartmouth College and Quechee Gorge Bridge.
Opens in a new windowAddie's Place: A Quiet and Quirky Guesthouse
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 NH
Located in Sunapee, this cottage is a 3-minute drive from Lake Sunapee and 7 minutes from Wendell Marsh Wildlife Management Area.
Opens in a new windowSweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Ludlow VT
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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Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock VT
With a stay at this cottage in Woodstock, you'll be on the waterfront, within a 15-minute drive of Quechee Gorge Bridge and Marsh-Billings-Rockefeller National ...
Opens in a new windowWoodstock Village Carriage House
Walk to Sunapee - Screened Porch Bliss + Cool AC

Walk to Sunapee - Screened Porch Bliss + Cool AC

Newbury NH
Located in Newbury (Blodgett Landing), this cottage is within a 5-minute drive of Lake Sunapee and The Fells.
Opens in a new windowWalk to Sunapee - Screened Porch Bliss + Cool AC
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 VT
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!
Cozy Crescent Cottage-Lakefront-Quiet- 25 min from Mt Sunapee -Pet friendly

Cozy Crescent Cottage-Lakefront-Quiet- 25 min from Mt Sunapee -Pet friendly

Lempster NH
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.
Opens in a new windowCozy Crescent Cottage-Lakefront-Quiet- 25 min from Mt Sunapee -Pet friendly
The Cairn,  1840s Cozy Stone Cottage, Pet Friendly

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Chester VT
Located in Chester, this cottage is within a 15-minute drive of Vermont Country Store and DaVallia Art & Accents.
Opens in a new windowThe Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Family & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee

Family & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee

Sunapee NH
Located in Sunapee, this cottage is on the waterfront, a 1-minute drive from Perkins Pond and 9 minutes from Wendell Marsh Wildlife Management Area.
Opens in a new windowFamily & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee
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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
89 Cottages
Lowest Price
AU$173
Highest Price
AU$552
Popular accommodation
Addie's Place: A Quiet and Quirky Guesthouse, Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee, Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit, Woodstock Village Carriage House, Walk to Sunapee - Screened Porch Bliss + Cool AC, Cozy cottage on the river, minutes from skiing, horse events, and so much more!, Cozy Crescent Cottage-Lakefront-Quiet- 25 min from Mt Sunapee -Pet friendly, The Cairn, 1840s Cozy Stone Cottage, Pet Friendly, Family & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee

Top trending hotels in Windsor

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
The price is AU$213 per night from 17 May to 18 May
AU$213
17 May - 18 May
includes taxes & fees
Located in West Lebanon, Fireside Inn & Suites West Lebanon is in a shopping district, a 2-minute drive from Connecticut River and 5 minutes from Upper Valley ...
Opens in a new windowFireside Inn & Suites West Lebanon
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$188 per night from 25 May to 26 May
AU$188
25 May - 26 May
includes taxes & fees
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 ...
Opens in a new windowKillington 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$173 per night from 18 May to 19 May
AU$173
18 May - 19 May
includes taxes & fees
When you stay at Align Inn Vermont in Quechee, you'll be in a state park, within a 15-minute drive of Quechee Gorge Bridge and Dartmouth College.
Opens in a new windowAlign 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$552 per night from 25 May to 26 May
AU$552
25 May - 26 May
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
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.