Hot Winchester Cottage Rates

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Featured Cottages in Winchester

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
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 ...
Opens in a new windowCottage 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
The price is AU$560 per night from 12 Nov to 13 Nov
AU$560
12 Nov - 13 Nov
includes taxes & fees
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.
Opens in a new window2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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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.
Opens in a new windowWaterfront Cottage on Scenic Sportsman Pond
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.
Opens in a new windowVacationer's oasis on the waterfront of picturesque Pearly Pond.
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

3 out of 5
Royalston
With a stay at this cottage in Royalston, you'll be within a 5-minute drive of Royalston State Forest and Royalston Falls.
Opens in a new windowHistoric Home w/ Modern Updates on < 4 Acres
Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac

2 out of 5
Rindge
The price is AU$519 per night from 12 Nov to 13 Nov
AU$519
12 Nov - 13 Nov
includes taxes & fees
Located in Rindge, this cottage is on a lake, a 1-minute drive from Wellington Park and 5 minutes from Rindge Historcal Museum.
Opens in a new windowFinnish Cabin with Sauna on Lake Monomonac
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3 out of 5
Wilmington
With a stay at this cottage in Wilmington, you'll be within a 10-minute drive of Lake Raponda and Green Mountain National Forest.
Opens in a new windowRustic Marlboro Cottage: 4 Mi to Lake Raponda!
Quaint Massachusetts Home w/ Yard & Grill!

Quaint Massachusetts Home w/ Yard & Grill!

3 out of 5
Gill
Located in Gill, this cottage is a 4-minute drive from Northfield Mount Hermon School and 5 minutes from Bernardston Town Hall.
Opens in a new windowQuaint Massachusetts Home w/ Yard & Grill!
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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
54 Cottages
Lowest Price
AU$143
Highest Price
AU$560
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Cottage on Partridge Pond, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Waterfront Cottage on Scenic Sportsman Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Historic Home w/ Modern Updates on < 4 Acres, Finnish Cabin with Sauna on Lake Monomonac, Rustic Marlboro Cottage: 4 Mi to Lake Raponda!, Quaint Massachusetts Home w/ Yard & Grill!

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
Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.
Opens in a new windowThe Colonial Hotel
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$143 per night from 12 Nov to 13 Nov
AU$143
12 Nov - 13 Nov
includes taxes & fees
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.
Opens in a new windowThe Covered Bridge Inn
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$154 per night from 7 Dec to 8 Dec
AU$154
7 Dec - 8 Dec
includes taxes & fees
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Opens in a new windowHampton Inn Brattleboro
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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$202 per night from 12 Nov to 13 Nov
AU$202
12 Nov - 13 Nov
includes taxes & fees
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 ...
Opens in a new windowColonial Motel And 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.