Pittsfield Holiday Rentals from NZ$226: Search Short-Term Rentals

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Our top choices for Pittsfield holiday rentals

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

Pittsfield

thomas v.

includes taxes & fees

5 Oct - 6 Oct

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

2. Angel Mist Retreat Garage Apartment

Pittsfield

Rob K.

includes taxes & fees

5 Oct - 6 Oct

3. Pine Tree Trail Lodge

Pittsfield

Amber G.

includes taxes & fees

2 Nov - 3 Nov

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

4. Pretty Old House in Newport

Newport

Sallie S.

includes taxes & fees

5 Oct - 6 Oct

A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

5. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Benton

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

18 Oct - 19 Oct

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.

includes taxes & fees

5 Oct - 6 Oct

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

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

Fairfield

Tonilynne D.

includes taxes & fees

5 Oct - 6 Oct

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.

9. Cozy House in the heart of Waterville Maine.

Waterville

Leslie G.

includes taxes & fees

5 Oct - 6 Oct

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

10. Sister A-Frame in Woods B

Oakland

Amanda M.

includes taxes & fees

2 Nov - 3 Nov

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

includes taxes & fees

12 Oct - 13 Oct

A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

12. Discover Oakland charm near Colby College 10 min

Oakland

Patricia

includes taxes & fees

25 Oct - 26 Oct

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

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

Sangerville

Judith L.

includes taxes & fees

5 Oct - 6 Oct

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

14. Forest Cabin w/ Stunning Wall of Windows

Jackson

Laura

includes taxes & fees

1 Nov - 2 Nov

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

15. The heart of the Belgrade Lakes

Oakland

Maureen

includes taxes & fees

7 Oct - 8 Oct

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

"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."

Cheri A.

includes taxes & fees

12 Oct - 13 Oct

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

Sangerville

Michelle W.

includes taxes & fees

6 Oct - 7 Oct

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.

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with a table and chairs, a view of a house, and a tree.

19. Minutes to Colby

Waterville

Shelly B.

includes taxes & fees

5 Oct - 6 Oct

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

20. Spacious modern living in a quite neighborhood

Madison

Donna B.

includes taxes & fees

12 Oct - 13 Oct

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Top Pittsfield Hotel Reviews

The Elmwood

8/10 Good

"Great"

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent

"The room was clean. The bathroom updated. Breakfast was amazing. Everything was there that you could possibly want. The attendant for breakfast kept all foods well stocked and the counters were clean. Air conditioning was perfect."

Canaan Motel

10/10 Excellent

"My wife and I stayed here while attending the Common Ground Fair. As far as we could tell, Neal alone orchestrated and performed all duties. He was very friendly and helpful. Our room was nice & clean and well kept. Comfortable bed! It’s a motel, so don’t expect frills. Nice grounds in back, with a seasonal pool. Trails into the woods. Quiet. Great stay. Will stay again. Thanks Neal!"

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

10/10 Excellent

"My husband, our best friends, and I just returned from a relaxing and fabulous 5 days at Fish Upon a Star cabins Where to begin.......first of all, the cabin is adorable: a spacious 4 bedroom, 2 bath cabin with every amenity you might need and then some! The cabin was immaculately clean, attractively decorated, with a gorgeous view of East Pond. The cabin is cozy, with a gas fireplace, to such an extent that we just wanted to hang out and relax in the cabin doing puzzles, reading, knitting, going for walks or just sitting around on the comfortable sofas and chatting. Amy was very quick to respond to my text about check in and made sure she knew she was available should we need anything......we didn't. We are already thinking about next year and will make our reservation today! You won't regret choosing this cabin as your destination spot. We sure didn't!"

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 favorite 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 depends 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 NZ$226 per night. Entering your travel dates in the search wizard you might find 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?

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95: This highly rated holiday home rental in Pittsfield 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 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.

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Check prices for these dates

Our top choices for Pittsfield holiday rentals

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

2. Angel Mist Retreat Garage Apartment

3. Pine Tree Trail Lodge

4. Pretty Old House in Newport

5. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

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

7. Peaceful, Spacious Lodge with Golf & Sunset Views

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

9. Cozy House in the heart of Waterville Maine.

10. Sister A-Frame in Woods B

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

12. Discover Oakland charm near Colby College 10 min

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

14. Forest Cabin w/ Stunning Wall of Windows

15. The heart of the Belgrade Lakes

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

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

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

19. Minutes to Colby

20. Spacious modern living in a quite neighborhood

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

The Elmwood

Holiday Inn Express & Suites Waterville - North by IHG

The Skowhegan By Kasa

Best Western Plus Waterville Grand Hotel

Hampton Inn Waterville

The Towne Motel

Budget Host Airport Inn

Canaan Motel

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

Find out more about Pittsfield

Frequently asked questions

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