Holiday Rentals in Pittsfield

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Holiday Rentals in Pittsfield

Postcard Cabins Blake Brook

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great way to escape for a few days! Everything basic you may need is provided which makes packing easy and low stress."
The price is €134
includes taxes & fees
28 Apr - 29 Apr
Postcard Cabins Blake Brook

Six-Bedroom Family Retreat Near Portsmouth w/ Hot tub, Theater

Six-Bedroom Family Retreat Near Portsmouth w/ Hot tub, Theater

Cedar Lodge condo with mountain & lake Winnipesauke views!

9.6 out of 10, Exceptional, (40)
"I stayed at Cedar Lodge while at ski races at Gunstock. I was by myself and the condo was perfect for me. The snacks and bottled water were a nice touch. It was a great visit.Thank You,Bruce"
The price is €145
includes taxes & fees
11 Apr - 12 Apr
Cedar Lodge condo with mountain & lake Winnipesauke views!

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

10.0 out of 10, Exceptional, (168)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.8 out of 10, Exceptional, (21)
"As a family of 6, our options are limited to 2 hotel rooms or a vacation property. This property exceeded all expectations. Perfect balance between feeling like a family vacation home and an elevated rental property without being full luxury with the typical higher price tag. Will definitely return. "
The price is €394
includes taxes & fees
20 Apr - 21 Apr
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

New Lakefront Home sleeps 14 with dock.

8.8 out of 10, Excellent, (61)
"Location is very convenient - grocery within a 10 min ride, easy access to the Lake, dining, and popular Winnipesaukee villages around the lake. The amenities were generous - including towels and linens at the location, travel shampoo/condition/soaps available, fully stocked kitchen with dish soap and other kitchen tools available. The kitchen is tight and the central artery of the house, which made it difficult with 12 people. I'd recommend bringing a mattress pad or something for the pull...
New Lakefront Home sleeps 14 with dock.

Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub

9.8 out of 10, Exceptional, (31)
"Roomy, sunny cape only 8 minutes to the slopes. The place was clean, bright, and had everything we needed. 10 minutes to Walmart or Hannaford for what we forgot to bring. Loved the claw foot tub with bubble bath and a view of snow covered pines. Thank you for sharing your home"
Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub

Lake Access, Mtn Views, Game Room, Hot Tub & More!

Lake Access, Mtn Views, Game Room, Hot Tub & More!

Lakefront Alton Bay Retreat w/ Dock Near Beaches!

9.6 out of 10, Exceptional, (4)
"Great location for us. We are going to a Camp Kabeyun reunion and it was very convenient. There was some cleanliness issues with crumbs and such but overall the property was great."
Lakefront Alton Bay Retreat w/ Dock Near Beaches!

Rustic Rose Cottage of Historic West Lebanon

10.0 out of 10, Exceptional, (16)
"Wonderful place to get away, read, reflect and write. "
The price is €202
includes taxes & fees
20 Apr - 21 Apr
Rustic Rose Cottage of Historic West Lebanon

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (30)
"Charming, clean and lovely place to stay. Owners were very easy to communicate with. Place was gorgeous. We had a great time. We would definitely stay here again and highly recommend it!!! "
The price is €411
includes taxes & fees
27 Apr - 28 Apr
Cozy, Pet-Friendly Escape Near Lake & Mountains

Secluded Waterfront Real Estate - Dams Beach

9.0 out of 10, Wonderful, (36)
"We stayed there for Laconia weekend 2024. 4 couples were very comfortable. The street up to a certain part to get to location is paved then dirt. The driveway dirt and rocks which is rough especially for motorcycle. Owner allowed easy early check in and we were able to park motorcycles in garage which was awesome. Home could use some maintenance but overall nice. The location was quiet and secluded. Only downfall with the location for us is distance not walkable to get to weirs strip which we...
Secluded Waterfront Real Estate - Dams Beach

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

9.8 out of 10, Exceptional, (97)
"The hosts are super attentive, communicative and the check in could not have been easier. The place was super clean with all utensils, plates and kitchen supplies. There is an extended dog leash in the backyard so your pup can explore safely. Overall would recommend, the fireplace in particular was amazing to use."
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (17)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is €256
includes taxes & fees
23 Apr - 24 Apr
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

The view-Enjoy Lake Winni both on & off the water-outdoor enthusiasts dream

2.5 star property
10.0 out of 10, Exceptional, (1)
"Amazing location and views on the lake. The property was super clean with everything we needed for a comfortable stay. We were in Gilford for a ski trip and we the house was located just 19 min away from the slopes! Great communication with the management that was very pro active giving checkin and checkout info. 100% recommend! "
The view-Enjoy Lake Winni both on & off the water-outdoor enthusiasts dream

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.8 out of 10, Excellent, (15)
"We stay. In Alton Bay each year for a couple of concerts at Bank of NH Pavilion in Gilford. We extend it by staying for a couple of days at Lake Winnipesaukee The motel is perfectly located close to the venue and on the lake for swimming and boating while visiting BNH Pavilion. The motel is in a pine grove and is lake front. It's "!old school " feel reminds of my childhood. It's clean and quite, but no thrills. Don't expect first class accommodations but if you like the feel of a...
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!

9.6 out of 10, Exceptional, (59)
"Great spot, close to the beach, but not too close. Stayed off season to attend an event at funspot arcade. Price was great. Rooms were good size and everything was clean and tastefully decorated. Wi-Fi worked great. Will definitely stay here again. Thanks "
The price is €211
includes taxes & fees
13 Apr - 14 Apr
Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!

Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

9.6 out of 10, Exceptional, (133)
"We really enjoyed our stay. The condo was comfortable, clean, had everything you needed and was in a great location. We enjoyed walking across the street to the lake and up the hill to go the concert next door. We were also a short drive from Weirs Beach. We had great communication and hope to stay there again."
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

Lakefront Home with Private Beach Access & Hot Tub

10.0 out of 10, Exceptional, (5)
"Alex was very helpful, constantly checking in. House was equipped with everything you may need. He even let us check in an hour early. Great spot to stay."
Lakefront Home with Private Beach Access & Hot Tub

Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

8.2 out of 10, Very good, (29)
"We had a great stay at this property. It was very conveniently located near Gunstock Ski Resort. The hot tub was perfect after a long day skiing and tubing. The home was clean and well-furnished."
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
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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Other types of properties in Pittsfield you may be interested in

The Centennial

4.0 star property
8.8 out of 10, Excellent, (934)
"Stayed here multiple times. Always lovely"
The price is €178
includes taxes & fees
13 Apr - 14 Apr
The Centennial

Steele Hill Resorts

3.0 star property
8.4 out of 10, Very good, (630)
"Pool and other fun activities."
The price is €183
includes taxes & fees
17 Apr - 18 Apr
Steele Hill Resorts

Fairfield Inn By Marriott Concord

2.5 star property
8.4 out of 10, Very good, (1000)
"Decent room, decent breakfast. Kind of a sketchy area. Rooms either face an extremely busy interstate or a garbage-filled area below train tracks. "
The price is €113
includes taxes & fees
26 Apr - 27 Apr
Fairfield Inn By Marriott Concord
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.

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

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

Six-Bedroom Family Retreat Near Portsmouth w/ Hot tub, Theater: This holiday home rental outside of Pittsfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Pittsfield?

Expedia has 3 holiday 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 holiday rental in Pittsfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsfield. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.