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 VT
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
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 NH
The price is AU$486 per night from 11 Feb to 12 Feb
AU$486
11 Feb - 12 Feb
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
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam NH
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
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Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Rindge NH
With a stay at this cottage in Rindge, you'll be on the waterfront, just steps from Pearly Lake and a 3-minute drive from Franklin Pierce University.
Opens in a new windowLakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

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

Rindge NH
When you 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 MA
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
Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster MA
Located in Westminster, this cottage is on the waterfront, within a 15-minute drive of 1761 Old Mill Gift Shop and Dunn State Park.
Opens in a new windowCottage on Partridge Pond
Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac

2 out of 5
Rindge NH
The price is AU$424 per night from 11 Feb to 12 Feb
AU$424
11 Feb - 12 Feb
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
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon MA
Located in Winchendon, this cottage is a 1-minute drive from Blueberry Island and 6 minutes from Winchendon Community Park.
Opens in a new windowModern Waterfront Gem w/ Dock on Lake Monomonac
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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
58 Cottages
Lowest Price
AU$177
Highest Price
AU$486
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Waterfront Cottage on Scenic Sportsman Pond, Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Historic Home w/ Modern Updates on < 4 Acres, Cottage on Partridge Pond, Finnish Cabin with Sauna on Lake Monomonac, Modern Waterfront Gem w/ Dock on Lake Monomonac

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
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 5 Mar to 6 Mar
AU$191
5 Mar - 6 Mar
includes taxes & fees
When you stay at Comfort Inn & Suites Brattleboro I-91 in Brattleboro, you'll be near ski lifts, within a 10-minute walk of Connecticut River and United States ...
Opens in a new windowComfort Inn & Suites Brattleboro I-91
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$177 per night from 1 Mar to 2 Mar
AU$177
1 Mar - 2 Mar
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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Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is AU$358 per night from 11 Mar to 12 Mar
AU$358
11 Mar - 12 Mar
includes taxes & fees
With a stay at Vikings Villages Resort in Brattleboro, you'll be 6.1 mi (9.8 km) from Vermont Marketplace and 7.5 mi (12.1 km) from The Stone Church.
Opens in a new windowVikings Villages 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.