Hot Winchester Cottage Rates

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Featured Cottages in Winchester

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Rindge
When you a stay at this cottage in Rindge, you'll be on the beach, just steps from Franklin Pierce University and Pearly Lake.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
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
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam
With a stay at this cottage in Fitzwilliam, you'll be on the waterfront, just steps from Sportsman Pond and a 4-minute drive from Lawrence Brook WMA.
Waterfront Cottage on Scenic Sportsman Pond
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Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster
With a stay at this cottage in Westminster, you'll be on the waterfront, within a 15-minute drive of Wachusett Mountain Ski Area and 1761 Old Mill Gift ...
Cottage on Partridge Pond
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Rindge
When you stay at this cottage in Rindge, you'll be on the waterfront, within a 5-minute drive of Contoocook Lake and Contoocook River.
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

Winchendon
With a stay at this cottage in Winchendon, you'll be within a 5-minute drive of Winchendon Community Park and Blueberry Island.
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

Walpole
The price is AU$464 per night from 24 Nov to 25 Nov
AU$464
includes taxes & fees
24 Nov - 25 Nov
Located in Walpole, this cottage is in a rural location, within a 10-minute drive of Connecticut River and Walpole Artisans Cooperative.
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
Finnish cottage with Sauna on Lake Monomonac

Finnish cottage with Sauna on Lake Monomonac

2 out of 5
Rindge
The price is AU$383 per night from 5 Dec to 6 Dec
AU$383
includes taxes & fees
5 Dec - 6 Dec
Located in Rindge, this cottage is on a lake, within a 10-minute drive of Rindge Historcal Museum and Betsy Fosket Wildlife Sanctuary.
Finnish cottage with Sauna on Lake Monomonac
Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Fitzwilliam
Located in Fitzwilliam, this cottage is on a lake, a 1-minute drive from Laurel Lake and 6 minutes from Sportsman Pond.
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
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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.

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

Winchester Cottages essential information

Accommodation
39 Cottages
Lowest Price
AU$125
Highest Price
AU$464
Popular accommodation
Vacationer's oasis on the waterfront of picturesque Pearly Pond., Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Waterfront Cottage on Scenic Sportsman Pond, Cottage on Partridge Pond, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula , Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions, Finnish cottage with Sauna on Lake Monomonac , Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Top trending hotels in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
The price is AU$240 per night from 5 Dec to 6 Dec
AU$240
includes taxes & fees
5 Dec - 6 Dec
Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.
The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 3 Dec to 4 Dec
AU$178
includes taxes & fees
3 Dec - 4 Dec
A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus ...
Colonial Motel And Spa
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$125 per night from 29 Nov to 30 Nov
AU$125
includes taxes & fees
29 Nov - 30 Nov
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 10-minute walk of Brattleboro Bowl and United States Navy Seabee Bridge.
The Covered Bridge Inn
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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 22 Dec to 23 Dec
AU$164
includes taxes & fees
22 Dec - 23 Dec
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
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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.