Holiday Rentals in Pittsfield

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Holiday Rentals in Pittsfield

The Barn - Lake View and Pet Friendly

The price is €225
includes taxes & fees
5 Aug - 6 Aug
The Barn - Lake View and Pet Friendly

The Cottages at Harvey Lake

3.0 star property
8.6 out of 10, Excellent, (44)
"The view of the lake from the cabin was excellent. "
The price is €126
includes taxes & fees
23 Jul - 24 Jul
The Cottages at Harvey Lake

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

9.0 out of 10, Wonderful, (19)
"Excellent"
The price is €247
includes taxes & fees
27 Jul - 28 Jul
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Newly Renovated Cottage 4 in Alton Bay, NH

8.8 out of 10, Excellent, (3)
"Communication was amazing, check in was a delightful, the house itself was perfect "
The price is €383
includes taxes & fees
28 Jul - 29 Jul
Newly Renovated Cottage 4 in Alton Bay, NH

Cozy hotel-style suite right on the water, shared patio, free WiFi

9.0 out of 10, Wonderful, (14)
"It is a very peaceful setting. "
The price is €250
includes taxes & fees
27 Jul - 28 Jul
Cozy hotel-style suite right on the water, shared patio, free WiFi

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

8.8 out of 10, Excellent, (16)
"Nice location on the lake."
The price is €274
includes taxes & fees
27 Jul - 28 Jul
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Luxurious Cabin in the Woods

10.0 out of 10, Exceptional, (2)
"Very nice clean quiet and private real cozy"
The price is €210
includes taxes & fees
5 Aug - 6 Aug
Luxurious Cabin in the Woods

The Village of Paugus Bay Studio Close To It All!

8.6 out of 10, Excellent, (4)
"Place looked just like the pictures. Owner was responsive"
The price is €254
includes taxes & fees
31 Jul - 1 Aug
The Village of Paugus Bay Studio Close To It All!

Cool New Dover Home

10.0 out of 10, Exceptional, (3)
"Beautiful home and the property manager answered any questions very quickly. Everything went without a hitch. Check-in was flawless, the house was immaculate and extremely comfortable. They left water in the fridge (which we didn’t need), cute little toothbrushes and toothpaste in the bathrooms along with combs, shampoo, condition and body wash. This house had everything of we had forgotten something. "
The price is €411
includes taxes & fees
5 Aug - 6 Aug
Cool New Dover Home

Newly Renovated Cottage 3 on Main Street Alton Bay!

The price is €420
includes taxes & fees
24 Jul - 25 Jul
Newly Renovated Cottage 3 on Main Street Alton Bay!

Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views

10.0 out of 10, Exceptional, (5)
The price is €492
includes taxes & fees
23 Jul - 24 Jul
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views

Stay in Venice our Modern Steps from the Lake with Dock!

10.0 out of 10, Exceptional, (6)
"Very clean and in a great location."
The price is €357
includes taxes & fees
4 Aug - 5 Aug
Stay in Venice our Modern Steps from the Lake with Dock!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

The price is €362
includes taxes & fees
5 Aug - 6 Aug
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cozy Cottage on a Lake, near Gunstock Mountain

10.0 out of 10, Exceptional, (1)
"The cabin is so cute and cozy! Very comfortable. We slept great! The neighbors were very friendly and even invited us over! The neighborhood is quiet and peaceful. The lake beach were amazing! We had a wonderful weekend getaway. The hosts are easy to contact. We will stay again! Love love the location! The only downside is there is no lake view from the cottage like we thought but easy lake access. We did not use the hot tub, washer/dryer or fire pit but those are great amenities! This place has...
The price is €369
includes taxes & fees
5 Aug - 6 Aug
Cozy Cottage on a Lake, near Gunstock Mountain

3bd2ba hot tub, concerts, lake, game room, fire pit

2.0 star property
10.0 out of 10, Exceptional, (2)
"Two family’s over night for 2 nights after an Old Dominion concert at Bank Pavilion. Only a 10 min drive , perfect location. House was super clean, kitchen was stalked so you could make meals, bedrooms were comfortable, kids (and adults!) loved the game room and we spent the most of our time on the amazing screened in porch. Communication with the hosts was so easy! We will absolutely come back to the hideaway! "
3bd2ba hot tub, concerts, lake, game room, fire pit

New Charming Chalet with Lake Winni Views

10.0 out of 10, Exceptional, (1)
"Great"
The price is €752
includes taxes & fees
30 Jul - 31 Jul
New Charming Chalet with Lake Winni Views

Room 8 (3rd Floor and Shared Bathroom)

9.4 out of 10, Exceptional, (13)
"Great place to stay. The owner is so nice."
The price is €230
includes taxes & fees
23 Jul - 24 Jul
Room 8 (3rd Floor and Shared Bathroom)

Waterfront Home w/ Private Dock

10.0 out of 10, Exceptional, (18)
"Our family had a wonderful time at this lake house. It had everything we needed for cooking, playing in the lake and relaxing. Would definitely stay again! "
The price is €351
includes taxes & fees
3 Aug - 4 Aug
Waterfront Home w/ Private Dock

Tranquil Summer Retreat – Lakeside Home & Hot Tub

10.0 out of 10, Exceptional, (22)
"Our girls weekend was perfect! The beds were super comfy, check-in was easy, the fireplace was ready to go and any and all communication with the hosts was pleasant and timely! Highly recommend! "
The price is €842
includes taxes & fees
24 Jul - 25 Jul
Tranquil Summer Retreat – Lakeside Home & Hot Tub

Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10

9.8 out of 10, Exceptional, (9)
"Overall our stay was good and owner is super responsive. "
The price is €747
includes taxes & fees
5 Aug - 6 Aug
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
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

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?

The Cottages at Harvey Lake: This holiday home rental outside of Pittsfield is located on the waterfront, and has a terrace, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchenette with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.