Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

The Barn - Lake View and Pet Friendly
6.0 out of 10, (1)
"It was peaceful and quiet, nice water view from the picture window , whole place was nice sized, Nice sized kitchen downstairs and office room, The main bathroom upstairs was nice and balcony was very nice, However the strong smell of animal urin all upstairs in the living room/bedroom was overwhelming, We brought our own lysol wipes to wipe everything down and used our Febreeze air spray to try to clean the smell upstairs , the little sofa looked stained and smelled, We sprayed it with...
United States
Joseph G.
The price is AU$292
includes taxes & fees
1 Nov - 2 Nov
The Barn - Lake View and Pet Friendly
Cozy RV in Wonderful Northwood with AC, WiFi, Kayaks & canoe!
9.0 out of 10, Wonderful, (2)
"Need a shower and table top fire pit."
United States
Sofia L.
The price is AU$205
includes taxes & fees
22 Oct - 23 Oct
Cozy RV in Wonderful Northwood with AC, WiFi, Kayaks & canoe!
The Coziest Tiny Home with Mini Cows & Horses!
9.4 out of 10, Exceptional, (19)
"Stayed for much needed adult getaway with my husband and it was exactly what we needed. It was quiet with everything we needed for a good time. We were able to bring our four-wheeler so that was nice. Looking out in the mornings with a coffee and watching the horses was so peaceful. I will definitely do this again! "
United States
Maranjellie A.
The price is AU$340
includes taxes & fees
31 Oct - 1 Nov
The Coziest Tiny Home with Mini Cows & Horses!
Fully stocked camper with delivery/setup to your favorite campground/cabin/event
6.0 out of 10, (1)
"The ad said the camper was nearly new, which it was not. We had a time to meet Jake, but he came and left early so we didn't get an intro. It was okay cleanliness wise, except the refrigerator was gross, and the shower curtain had dead bugs wrapped up in it. The cabinets were all very full, so we didn't have any place to put our food without moving stuff around. Then we had ants. The bed was very comfortable. We slept great. This is what we wanted it for, so wasn't disappointed in that. We used...
United States
Cathy M.
The price is AU$744
includes taxes & fees
4 Nov - 5 Nov
Fully stocked camper with delivery/setup to your favorite campground/cabin/event
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (68)
"Amazing place for getaway!"
United States
Wenhuan
The price is AU$315
includes taxes & fees
22 Oct - 23 Oct
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Cedar Lodge condo with mountain & lake Winnipesauke views!
9.6 out of 10, Exceptional, (50)
"Quiet comfortable room. "
United States
Olivia
The price is AU$266
includes taxes & fees
12 Nov - 13 Nov
Cedar Lodge condo with mountain & lake Winnipesauke views!
On Baxter Lake: Wooded Retreat Near Trails
3.0 star property
The price is AU$470
includes taxes & fees
23 Oct - 24 Oct
On Baxter Lake: Wooded Retreat Near Trails
Lake Winni 2BR Condo / Hiking/Pool/Tennis
10.0 out of 10, Exceptional, (1)
"We had a great stay! Great location and plenty of room for everyone. "
United States
Alicia O.
The price is AU$332
includes taxes & fees
2 Nov - 3 Nov
Lake Winni 2BR Condo / Hiking/Pool/Tennis
Newly Renovated Cottage 3 on Main Street Alton Bay!
10.0 out of 10, Exceptional, (1)
"Great little spot right next to the bay. Team was super responsive prior, during and after check in. Would highly recommend. "
United States
Andy S.
The price is AU$364
includes taxes & fees
2 Nov - 3 Nov
Newly Renovated Cottage 3 on Main Street Alton Bay!
Newly Remodeled Cedar Lodge Room w/ Lake Views!
9.4 out of 10, Exceptional, (19)
"Nice room perfect for what we were looking for"
United States
Terri D.
The price is AU$274
includes taxes & fees
17 Nov - 18 Nov
Newly Remodeled Cedar Lodge Room w/ Lake Views!
Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!
9.6 out of 10, Exceptional, (68)
"Great location, only 5 miles from our concert venue and off the main routes so it was quite quiet."
United States
VERNON
The price is AU$422
includes taxes & fees
22 Oct - 23 Oct
Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
9.0 out of 10, Wonderful, (22)
"Excellent"
United States
Diane L.
The price is AU$436
includes taxes & fees
26 Oct - 27 Oct
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Inviting condo in quiet locale with partial lake views, balcony & grilling area
8.4 out of 10, Very good, (17)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is AU$356
includes taxes & fees
4 Nov - 5 Nov
Inviting condo in quiet locale with partial lake views, balcony & grilling area
Taigh Loch - Lakes Region Retreat!
9.8 out of 10, Exceptional, (13)
"It was clean and comfortable. We enjoyed our stay. "
United States
Laurel C.
The price is AU$547
includes taxes & fees
22 Oct - 23 Oct
Taigh Loch - Lakes Region Retreat!
Walk to Concerts | Beach | Pool | Ski
8.0 out of 10, Very good, (12)
"Misty Harbor is a great place to stay when attending a concert at the NHIAA Bank Pavilion. Patti was a grew host, with great community. Her place was spotless!"
United States
Michael
The price is AU$302
includes taxes & fees
6 Nov - 7 Nov
Walk to Concerts | Beach | Pool | Ski
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
10.0 out of 10, Exceptional, (10)
"The house is superbly equipped and beautifully furnished. The host ist very friendly and easy to reach. We had a wonderful time. We loved the lake and the boats. "
Germany
Maja M.
The price is AU$635
includes taxes & fees
22 Oct - 23 Oct
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
8.6 out of 10, Excellent, (18)
"Nice location on the lake."
United States
Mary L.
The price is AU$482
includes taxes & fees
26 Oct - 27 Oct
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
☀ Bright and Charming Single-Family Home at Baxter Lake - Dog Friendly
9.8 out of 10, Exceptional, (23)
"Perfect place for a relaxing stay. Extremely well equipped and organized. Thank you for a wonderful stay"
United States
Carolyn D.
The price is AU$517
includes taxes & fees
4 Nov - 5 Nov
☀ Bright and Charming Single-Family Home at Baxter Lake - Dog Friendly
Newly Renovated Cottage 4 in Alton Bay, NH
9.0 out of 10, Wonderful, (4)
"Game room fun for all ages. "
United States
Anonymous traveller
The price is AU$560
includes taxes & fees
22 Oct - 23 Oct
Newly Renovated Cottage 4 in Alton Bay, NH
Rustic Rose Cottage of Historic West Lebanon
10.0 out of 10, Exceptional, (23)
"Beautiful, easy access, well appointed"
United States
Jeffrey J.
The price is AU$391
includes taxes & fees
20 Nov - 21 Nov
Rustic Rose Cottage of Historic West Lebanon
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

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$315 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Pittsfield is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.