Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Pittsfield

Property grounds
Pine Tree Trail Lodge

Holiday Home in Pittsfield

2.0 star property
The price is HK$1,266
HK$2,290 total
includes taxes & fees
15 Dec - 16 Dec
Pine Tree Trail Lodge
Fridge, microwave, oven, stovetop
Angel Mist Retreat Garage Apartment

Condo in Pittsfield

10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is HK$1,092
HK$2,402 total
includes taxes & fees
28 Dec - 29 Dec
Angel Mist Retreat Garage Apartment
Fridge, oven, stovetop, dishwasher
Classy AF Home Steps from Colby and Trails

Holiday Home in Oakland

10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails
Fridge, microwave, oven, stovetop
Large Secluded Cabin on the Lake - Now booking 2+ night stays

Cabin in Smithfield

10.0 out of 10, Exceptional, (66)
"Great vacation with 3 generations of our family. House was beautiful, lake clean with great swimming and fishing. Hope to return for years to come. "
United States
David M.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Fridge, microwave, oven, stovetop
Lakefront Cabin

Cabin in China

10.0 out of 10, Exceptional, (27)
"My family and I attended a concert at the Bowl in the Pines and wanted to make a weekend out of it and found this perfect little cabin right on the lake! Kids absolutely loved swimming, fishing and canoeing! Great spot for family bonding! Thank you! "
United States
Laura L.
Lakefront Cabin
Property grounds
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

Cabin in Exeter

10.0 out of 10, Exceptional, (134)
"Wonderful and very nice property. Owner more than gracious and hospitable. Would highly recommend."
United States
LMB
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Terrace/patio
The Cabin Skowhegan

Cabin in Skowhegan

9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is HK$778
HK$1,636 total
includes taxes & fees
6 Dec - 7 Dec
The Cabin Skowhegan
Exterior
Sister A-Frame in Woods B

Cabin in Oakland

10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$938
HK$1,776 total
includes taxes & fees
10 Dec - 11 Dec
Sister A-Frame in Woods B
Dining
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Holiday Home in Albion

9.8 out of 10, Exceptional, (37)
"Nice place, great fishing. "
United States
Bryan W.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Interior
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

Cabin in Dexter

10.0 out of 10, Exceptional, (23)
"We’ve enjoyed staying at this location!"
United States
Ted G.
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
Fridge, microwave, oven, stovetop
Lakefront cabin on North Pond with private beach

Cottage in Smithfield

9.6 out of 10, Exceptional, (7)
"We came to Maine to relax and decompress. This spot was perfect for that The quiet was just what we needed and the property was clean, spacious and comfortable."
United States
Michael C.
Lakefront cabin on North Pond with private beach
Fridge, microwave, oven, stovetop
The Hideout Cabin | Steps to the Beach

Cabin in Burnham

10.0 out of 10, Exceptional, (9)
"Amenities were great. Property was clean and quiet. Perfect for teens. Great view of the lake. Updated kitchen and grill was great for making family meals. Enjoyed making s'mores in the fire pit. Kayaks were so much fun. "
United States
Jamie M.
The price is HK$1,290
HK$3,437 total
includes taxes & fees
30 Nov - 1 Dec
The Hideout Cabin | Steps to the Beach
Interior
Family-friendly Troy Getaway With Furnished Deck!

Cottage in Troy

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great property and the owner was very welcoming and accommodating. Would recommend!!"
United States
Bonnie
Family-friendly Troy Getaway With Furnished Deck!
Property grounds
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

Cottage in Newport

10.0 out of 10, Exceptional, (121)
"It was a very nice place, clean, awesome view "
United States
Sharon D.
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Terrace/patio
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

Cabin in Exeter

9.8 out of 10, Exceptional, (166)
"host was great, beautiful cabin, great place quite, clean, lots to do , good hiking and wildlife, i give it a thumbs up for hikers "
United States
Felix M.
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
Interior
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Cabin in Oakland

9.2 out of 10, Wonderful, (26)
"Adorable cabin well stocked with plenty of space. Beautiful view! Nice and Clean. Needed help with the door lock and they were quick to respond and help. "
United States
Angela
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Smart TV
Cozy House in the heart of Waterville Maine.

Holiday Home in Waterville

9.6 out of 10, Exceptional, (49)
"Loved the cozy home! We would stay there again in a heartbeat. The only thing that we would have been nice is if there was a tv in the main bedroom, but that’s just a personal preference. "
United States
Michelle
Cozy House in the heart of Waterville Maine.
Dining
The Modern Maine Retreat

Holiday Home in Oakland

8.6 out of 10, Excellent, (13)
"Place was very clean, local to everything that we needed. Plenty of room for all 4 of us. I would definitely come back to this house if staying in Oakland again"
United States
Mark P.
The Modern Maine Retreat
Fridge, microwave, oven, stovetop
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

Holiday Home in Madison

9.6 out of 10, Exceptional, (72)
"A lovely stay as always. Beautiful lake and cozy camp. The sunrise is my favorite. "
United States
Joy S.
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Property grounds
Maplewood Lakehouse in Newport

Holiday Home in Newport

10.0 out of 10, Exceptional, (8)
"Maplewood Lakehouse was clean, spacious, accommodating, and everything our large group needed."
United States
Jane H.
Maplewood Lakehouse in Newport
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

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent
"Very Clean ! Staff was Extremely Nice and Helpful ! Breakfast was Wonderful ! Great Location - Very Close to Downtown and Colby College !"
Bradley 2-night trip
Posted 4 days ago
Holiday Inn Express & Suites Waterville - North by IHG

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:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

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

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. Pittsfield is known for its restaurants and shopping. Make sure you have time to check out the golf courses while you're in the area.

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

Pine Tree Trail Lodge: This highly rated holiday home rental in Pittsfield offers a fireplace, an arcade/games room and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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 can I see and do in Pittsfield?

Explore the area and family-friendly sights such as First Congregational Church, or get out into nature at a spot like Sebasticook Lake. JW Parks Golf Course and Skowhegan State Fairgrounds are a couple of places you'll find in the wider area.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.