Pittsfield Vacation Rentals

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Check prices for these dates

Tonight
Nov 27 - Nov 28
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Nov 28 - Nov 29
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Vacation Rentals in Pittsfield

Interior
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!

Cabin in Pittsfield

10.0 out of 10, Exceptional, (34)
"Even more beautiful than we were lead to hope for!Can’t wait to return with our entire family!"
United States
Mary Ann L.
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
Standard Cabin, 1 Queen Bed | Exterior
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Cabin in Epsom

2.0 star property
9.6 out of 10, Exceptional, (81)
"Everything was wonderful!!"
United States
Christina
The price is ￥14,468
￥22,475 total
includes taxes & fees
Dec 1 - Dec 2
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Marina
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Cabin in Alton

10.0 out of 10, Exceptional, (15)
"We thoroughly enjoyed our stay at your cozy, clean, comfy cabin. It was a fun place to spend our couple of days of vacation "
United States
Jackie r.
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Outdoor dining
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Cottage in Alton

8.6 out of 10, Excellent, (18)
"Location was A, however the overall place is very dated. One small pan to cook, along with a lobster pot. Furniture and bedding needs updating, along with interior. It is a great setting with lots of potential."
United States
Hubert B.
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Terrace/patio
New Lakefront Home sleeps 14 with dock.

Vacation Home in Alton

8.6 out of 10, Excellent, (67)
"We had such a nice time! The lake is gorgeous and everything we hoped for."
United States
Kirby L.
The price is ￥84,989
￥144,664 total
includes taxes & fees
Dec 26 - Dec 27
New Lakefront Home sleeps 14 with dock.
Terrace/patio
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Vacation Home in Alton

9.4 out of 10, Exceptional, (25)
"Perfect waterfront stay but did not like being so close to the road."
United States
Lucas T.
The price is ￥37,322
￥70,429 total
includes taxes & fees
Dec 3 - Dec 4
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Indoor pool
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Vacation Home in Gilford

9.8 out of 10, Exceptional, (178)
"Great place, beautiful view"
United States
Mike C.
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Fridge, microwave, oven, stovetop
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Vacation Home in Weirs Beach

10.0 out of 10, Exceptional, (15)
"Gathered for a family reunion! The house was great, plenty of common area to gather and spacious rooms. Brenda and Cliff were great hosts!"
United States
Kathi T.
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Beach
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

Cabin in Alton

9.6 out of 10, Exceptional, (14)
"Very neat place"
United States
Scott
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
TV
New Charming Chalet with Lake Winni Views

Vacation Home in Alton

9.4 out of 10, Exceptional, (3)
"Great house with a great location. Super responsive and having a slip to use makes the location perfect. "
United States
Ryan D.
New Charming Chalet with Lake Winni Views
Marina
Cabin with lake views & lake access Now featuring AC Wi-FI and TV sleeps 5

Cabin in Alton

9.4 out of 10, Exceptional, (9)
"Great place to stay! Tons of games and fire pits all around. I wish we had stayed longer to enjoy it all."
United States
Tara L.
Cabin with lake views & lake access Now featuring AC Wi-FI and TV sleeps 5
Fridge, microwave, oven, stovetop
Amazing lakefront retreat with stunning views - near skiing & golf

Vacation Home in Wolfeboro

7.0 out of 10, Good, (12)
"Could be a wonderful house but hasn't been taken care of. Location is great. Website did not clearly indicate the 83 steps from the house to the lake. Loved the association beach and amenities."
United States
Laurie W.
Amazing lakefront retreat with stunning views - near skiing & golf
Dining
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

Mobile Home in Gilford

9.8 out of 10, Exceptional, (16)
"We had a few hiccups the first day & night, however Colleen made it right.We would stay there again "
United States
Lisa M.
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing
Deluxe Apartment, Non Smoking | Private kitchen | Full-size fridge, microwave, oven, stovetop
9 Lake Street

Apartment in Wolfeboro

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
9 Lake Street
Outdoor spa tub
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

Vacation Home in Gilford

8.0 out of 10, Very Good, (44)
"The home was perfect for our stay! "
United States
Amy S.
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Exterior
Spacious New Hampshire mountain waterfront get away house. Boats & private docks

Vacation Home in Alton

9.8 out of 10, Exceptional, (44)
"This is a beautiful and tranquil destination. The kids loved fishing off of the dock (plenty of fish too!), swimming off the dock or at the nearby beach. Can’t wait to go back. "
United States
Nicole M.
Spacious New Hampshire mountain waterfront get away house. Boats & private docks
Exterior
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Vacation Home in Alton

10.0 out of 10, Exceptional, (1)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Exterior
Charming and spacious lakefront home with 4 bedrooms, hot tub and pool table!

Vacation Home in Farmington

10.0 out of 10, Exceptional, (61)
"Beautiful place, we had a great time. Everyone enjoyed themselves, and the lake was lovely! 10/10, would definitely recommend this place for a lake vacation "
United States
Lisa S.
Charming and spacious lakefront home with 4 bedrooms, hot tub and pool table!
Exterior
The Cottages at Harvey Lake

Vacation Home in Northwood

3.0 star property
8.8 out of 10, Excellent, (46)
"The cottage was great! It was very clean and comfy. The host had everything ready for us for a late check in. "
United States
Tonja
The Cottages at Harvey Lake
Beach nearby
Condo with WiFi, private beach, full kitchen, & outdoor pool

Condo in Gilford

7.8 out of 10, Good, (40)
"Great for a younger couple wanting a bargain spot close to the many local attractions."
United States
John P.
Condo with WiFi, private beach, full kitchen, & outdoor pool
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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Top Pittsfield Hotel Reviews

Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

10/10 Excellent
"The young man at the front desk was so friendly. We were able to bring our two dogs. We got a room at the end of the hall and that was very helpful when taking the dogs outside. "
Josephine 1-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Dover

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, there are vacation rentals close to popular local attractions in Pittsfield, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Pittsfield has to offer?

New Lakefront Home sleeps 14 with dock.: This vacation home rental outside of Pittsfield offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

How many vacation rentals will I find in Pittsfield?

Expedia has 3 vacation rentals for your stay in Pittsfield.

What’s there to see and do in Pittsfield?

Suncook River and Lily Lake are a couple of scenic spots to enjoy the outdoors, whereas Scenic Theatre is one of the cultural attractions. Other places in town to visit include Josiah Carpenter Library and Pittsfield Town Hall.

What’s a vacation rental in Pittsfield like?

Vacation rentals are private properties you can stay in for short or long periods in Pittsfield. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.