Pittsfield Vacation Rentals from $144: Search Short-Term Rentals

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Our top choices for Pittsfield vacation rentals

1. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

Pittsfield

thomas v.

$208 nightly

Oct 23 - Oct 24

Total with taxes and fees

A neatly made bed with white linens in a room with a wooden floor, a small wooden table, and a wall-mounted TV.

2. The Libby House – Fast WiFi, Parking & Full Kitchen

Pittsfield

$122 nightly

Oct 22 - Oct 23

Total with taxes and fees

A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

3. Angel Mist Retreat Garage Apartment

Pittsfield

Ruth W.

$282 nightly

Oct 24 - Oct 25

Total with taxes and fees

4. Pine Tree Trail Lodge

Pittsfield

Amber G.

$579 nightly

Nov 17 - Nov 18

Total with taxes and fees

A living room with a blue armchair, a beige armchair, a patterned rug, and a bookshelf with books and a plant.

5. Pretty Old House in Newport

Newport

Sallie S.

$286 nightly

Nov 14 - Nov 15

Total with taxes and fees

A cozy living room with a sofa, ottoman, and dining table with chairs. There are windows with curtains, a wooden ceiling, and a view of the outdoors.

6. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Canaan

Timothy S.

$397 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

7. Peaceful, Spacious Lodge with Golf & Sunset Views

Palmyra

Aaliya J.

$549 nightly

Oct 24 - Oct 25

Total with taxes and fees

A wooden cabin with a porch, a door, and a green chair.

8. Sister A-Frame in Woods B

Oakland

Amanda M.

$203 nightly

Nov 3 - Nov 4

Total with taxes and fees

A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

9. Charming cabin in the birches right on the atv trail!

Fairfield

Tonilynne D.

$140 nightly

Nov 19 - Nov 20

Total with taxes and fees

A two-story house with a wooden staircase and a balcony, two garage doors, and two ATVs parked in front.

10. New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville

Sangerville

Judith L.

$156 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern building with a black exterior and a large glass entrance.

11. Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Madison

Scott

$133 nightly

Oct 25 - Oct 26

Total with taxes and fees

A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

12. Cozy House in the heart of Waterville Maine.

Waterville

Leslie G.

$233 nightly

Nov 2 - Nov 3

Total with taxes and fees

A modern kitchen with a dining area, a sofa, and a window with a view.

13. Forest Cabin w/ Stunning Wall of Windows

Jackson

Laura

$222 nightly

Nov 1 - Nov 2

Total with taxes and fees

A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

14. The heart of the Belgrade Lakes

Oakland

"It was amazing! Shawna was great! I forgot to add our pet on the original booking and she was so responsive and we got everything sorted out. The apartment was so comfortable and decorated beautifully! Great space from kids room with things to entertain them to calm adult bedroom. The kitchen was well stocked and had everything you could think of. We loved “the fluffy butt hut” chicken coop!!! This is a dream place, from veggie garden, pool, tree house, chicken coop. Love it! Will definitely...

Tri C.

$215 nightly

Oct 22 - Oct 23

Total with taxes and fees

15. Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

Sangerville

Michelle W.

$288 nightly

Oct 30 - Oct 31

Total with taxes and fees

A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

16. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Smithfield

Sherrie

$150 nightly

Oct 23 - Oct 24

Total with taxes and fees

A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

17. Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Smithfield

Mike F.

$150 nightly

Oct 31 - Nov 1

Total with taxes and fees

A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

18. Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

Madison

Chase D.

$321 nightly

Oct 23 - Oct 24

Total with taxes and fees

A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

19. Spacious modern living in a quite neighborhood

Madison

Donna B.

$148 nightly

Oct 23 - Oct 24

Total with taxes and fees

A laundry room with a washing machine, dryer, and vacuum cleaner.

20. Dog Friendly, Steps to Lake, Golf, & Theate

Madison

Al Q.

$458 nightly

Nov 19 - Nov 20

Total with taxes and fees

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Top Pittsfield Hotel Reviews

Fireside Inn & Suites Waterville

8/10 Good

"It's centrally located, clean, basic, and a good, local restaurant connected. For such a quaint place, has fridge, hot tea or coffee in room, lock safe. Within minutes of some fine dining in downtown Waterville, which has free parking. Not plush, but clean, and basic. Good deal."

The Towne Motel

8/10 Good

"Highly recommend! We had a great stay! And hope to return. The Staff and Owner were fantastic! Helpful, professional & courteous. That plus a reasonable rate. You can’t go wrong. Book a stay and see for yourself. If you’re thinking about the over-rated Kasa, forget it and stay at a truly comfortable Casa. The Towne Motel. Thanks Dennis and staff."

The Skowhegan By Kasa

10/10 Excellent

"What a unique and beautiful place to stay in Skowhegan! We were able to go the restaurant in the building for dinner and walk to get coffee in town in the morning before we left. We highly recommend. The walls are a little thin so keep that in mind when there is an active community staying there."

Budget Host Airport Inn

10/10 Excellent

"I really enjoyed staying here and will definitely book a room in the future. The room was very comfortable, easy access, the television had a lot of channels. I couldn't hear anything from the other rooms. The bathroom was very clean. It was easy to park and the staff were available if I had any questions."

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

10/10 Excellent

"Having never been here before, I was surprised by how easy they made it to find the property. The driveway down to the house is NOT paved but safe to drive down. It’s not steep or slick. In the winter months however , I would make sure 4 wheel drive is an option. The cabin is, I’m not kidding you, perfect. It has kayaks, two docks to fish from. A sandy area near the dock to go into the water without having to worry about a weedy bottom. The view is amazing on the water when the morning fog clears. It’s quite literally like something from a movie. The host was not overbearing like some can be. The house rules are easy to both find and follow. The firewood was not something I knew about until AFTER my trip was over. Only because the magnet holding the posted rules on the fridge was in the way. Boy was I embarrassed. I was buying firewood the whole weekend haha. 10/10 would recommend and stay here again. I’m going to make it a tradition to come here yearly with my boys."

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $144 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation 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 vacation.

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.

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Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we have vacation rentals near popular points of interest in Pittsfield, or you can select a more remote option if you're looking for relaxation. 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's the top vacation rental in Pittsfield?

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95: Visitors like this Pittsfield vacation home rental. It offers a patio, a selection of books, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals will I find in Pittsfield?

Expedia has 3 vacation 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 larger area.

What are vacation rentals like in Pittsfield?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.

Pittsfield Vacation Rentals

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Check prices for these dates

Our top choices for Pittsfield vacation rentals

1. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

2. The Libby House – Fast WiFi, Parking & Full Kitchen

3. Angel Mist Retreat Garage Apartment

4. Pine Tree Trail Lodge

5. Pretty Old House in Newport

6. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

7. Peaceful, Spacious Lodge with Golf & Sunset Views

8. Sister A-Frame in Woods B

9. Charming cabin in the birches right on the atv trail!

10. New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville

11. Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

12. Cozy House in the heart of Waterville Maine.

13. Forest Cabin w/ Stunning Wall of Windows

14. The heart of the Belgrade Lakes

15. Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

16. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

17. Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

18. Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

19. Spacious modern living in a quite neighborhood

20. Dog Friendly, Steps to Lake, Golf, & Theate

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Fireside Inn & Suites Waterville

Find out more about Pittsfield

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