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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Pittsfield

Angel Mist Retreat Garage Apartment

10.0 out of 10, Exceptional, (14)
"Beautifully presented. Exceptionally well equipped ."
The price is AU$469
includes taxes & fees
8 Oct - 9 Oct
Angel Mist Retreat Garage Apartment

Family, Friends and Fun for all

2.0 star property
9.4 out of 10, Exceptional, (8)
"The property was very nice. Lots of rooms, fun environment, prompt communication. Worked great for our group."
Family, Friends and Fun for all

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

10.0 out of 10, Exceptional, (64)
"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

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

9.4 out of 10, Exceptional, (61)
"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

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.

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 AU$350
includes taxes & fees
13 Oct - 14 Oct
Sister A-Frame in Woods B

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

10.0 out of 10, Exceptional, (131)
"We had a family gathering in the area and this was perfect for our family of 4. "
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

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

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

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

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (46)
"Clean, comfortable and incredibly close to campus for a college visit."
Classy AF Home Steps from Colby and Trails

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

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

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

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. "
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

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

10.0 out of 10, Exceptional, (19)
"Great stay, the place is wonderful and the host is fantastic looking forward to staying again in the future "
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

The Modern Maine Retreat

8.6 out of 10, Excellent, (13)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

Minutes to Colby

8.6 out of 10, Excellent, (18)
"This was such a wonderful option. Location, clean, and adorable. "
The price is AU$292
includes taxes & fees
8 Oct - 9 Oct
Minutes to Colby

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

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

Lakefront Getaway with Kayak, Canoe, Boat and dock

9.2 out of 10, Wonderful, (7)
"We enjoyed our stay in Harmony. The perfect location for paddling and fishing"
Lakefront Getaway with Kayak, Canoe, Boat and dock
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

Find out more about Pittsfield

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$292 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. 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?

Family, Friends and Fun for all: This highly rated holiday home rental in Pittsfield is located in the mountains, and has a patio, a garden and a BBQ to put you at ease 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. Make the most of games in this rental home to help you unwind.

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.