Pittsfield Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Pittsfield

Angel Mist Retreat Garage Apartment
Exterior

Angel Mist Retreat Garage Apartment

10.0 out of 10, Exceptional, (14)
"Beautifully presented. Exceptionally well equipped ."
The price is HK$1,093
HK$2,396 total
includes taxes & fees
19 Oct - 20 Oct
Angel Mist Retreat Garage Apartment
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Fridge, microwave, oven, stovetop

Large Secluded Cabin on the Lake - Now booking 2+ night stays

10.0 out of 10, Exceptional, (65)
"Great location! Amy is a fantastic host and she has provided everything for a relaxing stay on East Pond. "
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Property grounds

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

10.0 out of 10, Exceptional, (131)
"Great small cabin in a really cute area! Super quiet and so peaceful for a nice weekend getaway. Debbie was so kind with check in and always available. Would definitely stay here again!"
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (63)
"Great family camp right on the water with great views and paddle boats to play and fish the lake. Nice host, it was a peaceful stay!"
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
Terrace/patio

Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

9.8 out of 10, Exceptional, (163)
"Beautiful, peaceful location. This was the perfect place to stay while my family was waiting for our house to be ready."
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Dining

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

9.8 out of 10, Exceptional, (37)
"Cute house with deck overlooking the pond with almost daily sightings of eagles, loons and ducks. We loved it here and would stay here again if we come back this way again. I hated to leave this cute home. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Cozy House in the heart of Waterville Maine.
Smart TV

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (45)
"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. "
Cozy House in the heart of Waterville Maine.
The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (49)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
The price is HK$778
HK$1,637 total
includes taxes & fees
17 Oct - 18 Oct
The Cabin Skowhegan
Classy AF Home Steps from Colby and Trails
Fridge, oven, stovetop, dishwasher

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
Classy AF Home Steps from Colby and Trails
Lakefront Cabin
Fridge, microwave, oven, stovetop

Lakefront Cabin

10.0 out of 10, Exceptional, (27)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Lakefront Cabin
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
Interior

Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

10.0 out of 10, Exceptional, (20)
"We’ve enjoyed staying at this location!"
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
Blake's Cabin
Exterior

Blake's Cabin

9.6 out of 10, Exceptional, (23)
"Had a great stay. Quiet and peaceful week on the lake"
The price is HK$1,518
HK$2,833 total
includes taxes & fees
14 Oct - 15 Oct
Blake's Cabin
Week discount. RV on 265 ac parcel with 15 Mile Stream running thru the property
Outdoor dining

Week discount. RV on 265 ac parcel with 15 Mile Stream running thru the property

9.6 out of 10, Exceptional, (4)
"Very quiet with so much wildlife and things to do, the host is awesome and very responsive to your needs."
Week discount. RV on 265 ac parcel with 15 Mile Stream running thru the property
Charming cabin in the birches right on the atv trail!
Smart TV

Charming cabin in the birches right on the atv trail!

2.0 star property
9.0 out of 10, Wonderful, (6)
"I felt very comfortable. It's a very nice cabin, it has all the amenities, and it's perfect for sharing as a couple or as a family. I had a great time."
Charming cabin in the birches right on the atv trail!
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Property grounds

10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

10.0 out of 10, Exceptional, (121)
"This is an excellent 1 bedroom vacation cabin on Lake Sebasticook. We had everything we needed for a nice stay."
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (6)
"Great stay. Would stay here again if in the area."
The price is HK$939
HK$1,778 total
includes taxes & fees
15 Oct - 16 Oct
Sister A-Frame in Woods B
Maplewood Lakehouse in Newport
Property grounds

Maplewood Lakehouse in Newport

10.0 out of 10, Exceptional, (7)
"The Maplewood Lakehouse is the PERFECT spot to gather with friends and family! The home itself is huge and inviting, but it's location to the town of Newport for gas, groceries, and take-out make it really stand out. This home has SO many bedrooms to accomodate our large group. We really appreciated having spaces to both be together (multiple living rooms, the game room/garage, and the kitchen/dining spaces) as well as the many bedrooms to have quiet space to recharge as well. And that's just...
Maplewood Lakehouse in Newport
Lakefront cabin on North Pond with private beach
Fridge, microwave, oven, stovetop

Lakefront cabin on North Pond with private beach

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."
Lakefront cabin on North Pond with private beach
Charming historic guest house on farm 3 bedrooms wood stove pet friendly
Exterior

Charming historic guest house on farm 3 bedrooms wood stove pet friendly

10.0 out of 10, Exceptional, (7)
"Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! "
The price is HK$1,662
HK$2,743 total
includes taxes & fees
14 Oct - 15 Oct
Charming historic guest house on farm 3 bedrooms wood stove pet friendly
Lakefront dog friendly cottage w/ a dock & beautiful sunset views
Property grounds

Lakefront dog friendly cottage w/ a dock & beautiful sunset views

8.0 out of 10, Very good, (1)
"Lovely lakeside cottage suited our needs nicely!!"
Lakefront dog friendly cottage w/ a dock & beautiful sunset views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

10/10 Excellent
"An excellent location and very enjoyable setting on the pond. Great place to sit outside and enjoy coffee in the morning and a glass of wine in the evening."
Bill M. 3-night trip
Posted 5 days ago
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

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?

Cozy House in the heart of Waterville Maine.: This holiday home rental outside of Pittsfield is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.