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 ...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Beautiful Modern Cottage with Sauna on Lake Monomonac

Beautiful Modern Cottage with Sauna on Lake Monomonac

2 out of 5
Rindge
The price is AU$489 per night from 2 Mar to 3 Mar
AU$489
includes taxes & fees
2 Mar - 3 Mar
Located in Rindge, this cottage is a 1-minute drive from Wellington Park and 5 minutes from Rindge Historcal Museum.
Beautiful Modern Cottage with Sauna on Lake Monomonac
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 Great Wolf Lodge Waterpark and 1761 Old Mill Gift Shop.
Cottage on Partridge Pond
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Finnish cottage with Sauna on Lake Monomonac

Finnish cottage with Sauna on Lake Monomonac

2 out of 5
Rindge
The price is AU$384 per night from 24 Feb to 25 Feb
AU$384
includes taxes & fees
24 Feb - 25 Feb
Located in Rindge, this cottage is on a lake, a 1-minute drive from Wellington Park and 5 minutes from Rindge Historcal Museum.
Finnish cottage with Sauna on Lake Monomonac
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
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.
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
Charming Jaffrey Cottage w/ Deck & Grill!

Charming Jaffrey Cottage w/ Deck & Grill!

Jaffrey
With a stay at this cottage in Jaffrey, you'll be in the mountains, just steps from Shattuck Golf Course and a 2-minute drive from Monadnock Reservation.
Charming Jaffrey Cottage w/ Deck & Grill!
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$392 per night from 24 Feb to 25 Feb
AU$392
includes taxes & fees
24 Feb - 25 Feb
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
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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
40 Cottages
Lowest Price
AU$169
Highest Price
AU$489
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Beautiful Modern Cottage with Sauna on Lake Monomonac, Cottage on Partridge Pond, Finnish cottage with Sauna on Lake Monomonac , Waterfront Cottage on Scenic Sportsman Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Charming Jaffrey Cottage w/ Deck & Grill!, Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

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$246 per night from 24 Feb to 25 Feb
AU$246
includes taxes & fees
24 Feb - 25 Feb
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$189 per night from 24 Feb to 25 Feb
AU$189
includes taxes & fees
24 Feb - 25 Feb
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
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$184 per night from 3 Mar to 4 Mar
AU$184
includes taxes & fees
3 Mar - 4 Mar
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 ...
Comfort Inn & Suites Brattleboro I-91
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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$169 per night from 11 Mar to 12 Mar
AU$169
includes taxes & fees
11 Mar - 12 Mar
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.