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Featured Cottages in Pittsfield

Cozy, Pet-Friendly Escape Near Lake & Mountains

Cozy, Pet-Friendly Escape Near Lake & Mountains

Gilford
The price is AU$714 per night from 27 Apr to 28 Apr
AU$714
includes taxes & fees
27 Apr - 28 Apr
When you stay at this cottage in Gilford, you'll be on a lake, within a 15-minute drive of Lake Winnipesaukee and Bank of New Hampshire Pavilion at ...
Cozy, Pet-Friendly Escape Near Lake & Mountains
Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon

Lebanon
The price is AU$355 per night from 20 Apr to 21 Apr
AU$355
includes taxes & fees
20 Apr - 21 Apr
Located in Lebanon, this cottage is in a rural location, within a 10-minute drive of East Rochester Public Library and Milton Three Ponds.
Rustic Rose Cottage of Historic West Lebanon
Cottage with great beach.

Cottage with great beach.

2 out of 5
Wolfeboro
With a stay at this cottage in Wolfeboro, you'll be on a lake, within a 10-minute drive of Lake Winnipesaukee and New Hampshire Boat Museum.
Cottage with great beach.
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Walk to Marina: Cute Gilford Cottage w/ Grill

Walk to Marina: Cute Gilford Cottage w/ Grill

Gilford
With a stay at this cottage in Gilford, you'll be a 2-minute drive from Lake Winnipesaukee and 6 minutes from Bank of New Hampshire Pavilion at Meadowbrook.
Walk to Marina: Cute Gilford Cottage w/ Grill
Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes

Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes

Wolfeboro
With a stay at this cottage, you'll be centrally located in Wolfeboro, within a 10-minute drive of Lake Winnipesaukee and Wolfeboro Institute of the Arts.
Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Gilmanton
The price is AU$437 per night from 7 May to 8 May
AU$437
includes taxes & fees
7 May - 8 May
Located in Gilmanton, this cottage is within a 15-minute drive of Gilmanton Public Library and Gilmanton Year-Round Library.
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Winnipesaukee house
w/ dock included.

Winnipesaukee house w/ dock included.

Laconia
With a stay at this cottage in Laconia (Bayside), you'll be within a 10-minute drive of Lake Winnipesaukee and Bank of New Hampshire Pavilion at ...
Winnipesaukee house w/ dock included.
Waterfront Cottage, Quiet and Secluded, on Swains Lake

Waterfront Cottage, Quiet and Secluded, on Swains Lake

Barrington
With a stay at this cottage in Barrington, you'll be on the waterfront, within a 15-minute drive of University of New Hampshire and Stonehouse Forest.
Waterfront Cottage, Quiet and Secluded, on Swains Lake
Cozy Lake Winnisquam retreat for 6 with dock and swimming

Cozy Lake Winnisquam retreat for 6 with dock and swimming

Meredith
Located in Meredith, this cottage is a 1-minute drive from Lake Winnisquam and 8 minutes from Wickwas Lake.
Cozy Lake Winnisquam retreat for 6 with dock and swimming
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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.

Pittsfield 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 Pittsfield 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 Pittsfield 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 Pittsfield, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Pittsfield Cottages essential information

Accommodation
121 Cottages
Lowest Price
AU$185
Highest Price
AU$714
Popular accommodation
Cozy, Pet-Friendly Escape Near Lake & Mountains, Rustic Rose Cottage of Historic West Lebanon, Cottage with great beach., Walk to Marina: Cute Gilford Cottage w/ Grill, Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes, Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit, Winnipesaukee house w/ dock included. , Waterfront Cottage, Quiet and Secluded, on Swains Lake, Cozy Lake Winnisquam retreat for 6 with dock and swimming

Top trending hotels in Pittsfield

The Centennial

The Centennial

4 out of 5
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is AU$313 per night from 13 Apr to 14 Apr
AU$313
includes taxes & fees
13 Apr - 14 Apr
Located in Concord, The Centennial is in the suburbs, within a 15-minute walk of New Hampshire Hospital Scorecard and New Hampshire State House.
The Centennial
Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is AU$322 per night from 4 May to 5 May
AU$322
includes taxes & fees
4 May - 5 May
With a stay at Steele Hill Resorts in Sanbornton, you'll be 4.7 mi (7.6 km) from Lake Winnisquam and 9.6 mi (15.5 km) from Funspot Family Fun Center.
Steele Hill Resorts
Fairfield Inn By Marriott Concord

Fairfield Inn By Marriott Concord

2.5 out of 5
4 Gulf St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 26 Apr to 27 Apr
AU$199
includes taxes & fees
26 Apr - 27 Apr
A stay at Fairfield Inn By Marriott Concord places you in the heart of Concord, within a 15-minute walk of Capitol Center for the Arts and Terrill Dog Park.
Fairfield Inn By Marriott Concord
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Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street, Laconia, NH
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 14 Apr to 15 Apr
AU$185
includes taxes & fees
14 Apr - 15 Apr
Located in Laconia, Best Western Plus Landmark Inn is a 4-minute drive from Paugus Bay and 12 minutes from Tanger Outlets Tilton.
Best Western Plus Landmark 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.