Search Condos Rentals in Pittsfield from CA $107

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Check prices for these dates

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Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Pittsfield condo rentals

A bedroom with a large bed, a ship's wheel wall decoration, and a view to the outside.

1. 1 Bedroom Lake Winnipesaukee Condo

1 Bedroom Lake Winnipesaukee Condo
Gilford
9.6 out of 10, Exceptional, (32 reviews)
"Great experience"
United States
Radu
The price is CA $168
CA $362 total
includes taxes & fees
Nov 7 - Nov 8
1 Bedroom Lake Winnipesaukee Condo
A lakeside patio with picnic tables, benches, and a view of the water.

2. Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.8 out of 10, Exceptional, (35 reviews)
"Great location, specially for concerts or enjoying the beach. Some road noise."
United States
Estuardo
The price is CA $201
CA $378 total
includes taxes & fees
Nov 16 - Nov 17
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.

3. Weirs beach retreat

Weirs beach retreat
Weirs Beach
9.8 out of 10, Exceptional, (8 reviews)
"Just a minutes drive to the waterfront and shops. Great location "
United States
Wayne W.
The price is CA $147
CA $379 total
includes taxes & fees
Nov 7 - Nov 8
Weirs beach retreat
A kitchen with a granite countertop, white cabinets, a built-in stove, and a hanging light fixture.

4. Lake Winni Waterfront Condo

Lake Winni Waterfront Condo
Gilford
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful spot! Walked to the Bank of NH venue for concert. Lake is beautiful. Beds are comfortable. Places adorable everything you need."
United States
Julie Larrivee P.
The price is CA $266
CA $501 total
includes taxes & fees
Nov 8 - Nov 9
Lake Winni Waterfront Condo
A two-story house with a dark roof, multiple windows, and a porch with chairs.

5. Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available

Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available
Wolfeboro
7.2 out of 10, Good, (5 reviews)
"No way does this deserve a 10/10 rating. It’s fairly terrible and not deserving such a favorable rating. The pluses - great location, right on the lake. Adirondacks at sunset was heavenly. Super convenient. Wolfeboro is very cute. The shower has been nicely redone. The in-unit washer/dryer worked well and was very convenient. But the negatives are many. Lots of disrepair and terrible attention to detail. We got a spongy soft double bed. The listing says Queen bed. It’s not. We had badly stained...
United States
Brian L.
The price is CA $198
CA $388 total
includes taxes & fees
Nov 8 - Nov 9
Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available
A residential area with multiple buildings, a lake, and mountains in the background.

6. Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach

Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach
Weirs Beach
10.0 out of 10, Exceptional, (3 reviews)
"Good location with clean and comfortable beds. Thx!"
United States
Phil C.
The price is CA $140
CA $285 total
includes taxes & fees
Nov 8 - Nov 9
Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach
A two-story motel with a flat roof, located near a lake with a forested backdrop.

7. Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi

Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi
Weirs Beach
9.6 out of 10, Exceptional, (5 reviews)
"Condo was very clean, rooms her good sized, each having a separate bathroom was ideal. Also centrally located for attending Laconia bike week. About 4 miles from Weirs beach, walking distance to Cumberland Farms. The host, Margaret, was exceptional. Would highly recommend."
United States
Darren
The price is CA $126
CA $446 total
includes taxes & fees
Nov 9 - Nov 10
Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi
A balcony with a view of a river and buildings, a wooden ceiling, and a window with a curtain.

8. Lakes Region Escape | Private Balcony Near Weirs Beach

Lakes Region Escape | Private Balcony Near Weirs Beach
Weirs Beach
10.0 out of 10, Exceptional, (1 review)
"Great location. Close to the strip"
United States
Adam C.
The price is CA $140
CA $285 total
includes taxes & fees
Nov 8 - Nov 9
Lakes Region Escape | Private Balcony Near Weirs Beach
A balcony with a view of a river and buildings, a wooden ceiling, and a window with a curtain.

9. Lakes Region Getaway | 3BR Condo Near Weirs Beach

Lakes Region Getaway | 3BR Condo Near Weirs Beach
Weirs Beach
The price is CA $155
CA $303 total
includes taxes & fees
Nov 8 - Nov 9
Lakes Region Getaway | 3BR Condo Near Weirs Beach
A rooftop deck with outdoor furniture, a pool, and a view of the surrounding area.

10. Inviting 1BR Lakeview 2nd-Floor - Balcony

Inviting 1BR Lakeview 2nd-Floor - Balcony
Gilford
8.4 out of 10, Very good, (17 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is CA $108
CA $371 total
includes taxes & fees
Nov 7 - Nov 8
Inviting 1BR Lakeview 2nd-Floor - Balcony
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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Learn more about Pittsfield

Explore attractions like Scenic Theatre and Josiah Carpenter Library as you discover things to see and do in Pittsfield.

See all hotels in Pittsfield
A calm lake reflecting colorful autumn trees and misty mountains in the distance.

Top reviews in Pittsfield

A spacious living room with a fireplace, comfortable seating, and a modern chandelier.
The Hotel Concord

The Hotel Concord

The Hotel Concord
Downtown Concord

10/10 Excellent

Staff very friendly and helpful. Parking efficient and easy access.
Canada
Peter
Reviewed April 16, 2026
The Hotel Concord

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