Hot Winchester Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Winchester

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.
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole
The price is AU$404 per night from 3 Apr to 4 Apr
AU$404
includes taxes & fees
3 Apr - 4 Apr
Located in Walpole, this cottage is in a rural location, within a 10-minute drive of Connecticut River and Walpole Artisans Cooperative.
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Save an average of 15% on thousands of hotels when you're signed in
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
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
Finnish cottage with Sauna on Lake Monomonac

Finnish cottage with Sauna on Lake Monomonac

2 out of 5
Rindge
The price is AU$525 per night from 3 Apr to 4 Apr
AU$525
includes taxes & fees
3 Apr - 4 Apr
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
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$598 per night from 3 Apr to 4 Apr
AU$598
includes taxes & fees
3 Apr - 4 Apr
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
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Newfane
Located in Newfane, this cottage is in a rural location, a 3-minute drive from Rock River Preserve and 7 minutes from West River.
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
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
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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
49 Cottages
Lowest Price
AU$162
Highest Price
AU$598
Popular accommodation
Waterfront Cottage on Scenic Sportsman Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Finnish cottage with Sauna on Lake Monomonac , Beautiful Modern Cottage with Sauna on Lake Monomonac, Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow, Cottage on Partridge Pond

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$244 per night from 3 Apr to 4 Apr
AU$244
includes taxes & fees
3 Apr - 4 Apr
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
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$187 per night from 28 Apr to 29 Apr
AU$187
includes taxes & fees
28 Apr - 29 Apr
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
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$191 per night from 3 Apr to 4 Apr
AU$191
includes taxes & fees
3 Apr - 4 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd, Putney, VT
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 3 Apr to 4 Apr
AU$162
includes taxes & fees
3 Apr - 4 Apr
With a stay at The Putney Inn in Putney, you'll be a 4-minute walk from Connecticut River and 8 minutes by foot from Yellow Barn.
The Putney Inn
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.