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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
Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster
Located in Westminster, this cottage is on the waterfront, within a 15-minute drive of 1761 Old Mill Gift Shop and Dunn State Park.
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
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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
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
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
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.
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 5-minute drive from Jaffrey Civic Center.
Charming Jaffrey Cottage w/ Deck & Grill!
Lakeside living!  Relax and enjoy prestine Granite Lake…..your oasis to breathe

Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

Stoddard
Located in Nelson, this cottage is within a 15-minute drive of Granite Gorge and Highland Lake.
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
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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
38 Cottages
Lowest Price
AU$163
Highest Price
AU$250
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, VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula , Waterfront Cottage on Scenic Sportsman Pond, Cottage on Laurel Lake, Private lake access, picture perfect sunsets, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Charming Jaffrey Cottage w/ Deck & Grill!, Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

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$250 per night from 24 Dec to 25 Dec
AU$250
includes taxes & fees
24 Dec - 25 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$172 per night from 1 Jan to 2 Jan
AU$172
includes taxes & fees
1 Jan - 2 Jan 2025
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
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$163 per night from 12 Jan to 13 Jan
AU$163
includes taxes & fees
12 Jan - 13 Jan 2025
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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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$201 per night from 6 Jan to 7 Jan
AU$201
includes taxes & fees
6 Jan - 7 Jan 2025
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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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.