Holiday Rentals in Pittsfield

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Holiday Rentals in Pittsfield

Family, Friends and Fun for all

2.0 star property
9.4 out of 10, Exceptional, (3)
"We booked this location for our workers for the 2025 Master Amateur Invitational due to its proximity to the event grounds. The place was amazing and perfect for this event. The staff and the hosts were very responsive and accommodating to all our needs. I would recommend this place to anyone staying in the Pittsfield, ME area."
The price is €354
includes taxes & fees
24 Aug - 25 Aug
Family, Friends and Fun for all

Angel Mist Retreat Garage Apartment

10.0 out of 10, Exceptional, (11)
"Wonderful apartment in all ways. Wonderfully outfitted. Beautiful environs. "
The price is €272
includes taxes & fees
14 Aug - 15 Aug
Angel Mist Retreat Garage Apartment

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

10.0 out of 10, Exceptional, (126)
"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, (160)
"Great place with nice hosts! They were very helpful "
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

Large Secluded Cabin on the Lake - NOW SLEEPS 10

10.0 out of 10, Exceptional, (57)
"Would stay there again in a heartbeat, above our expectations "
Large Secluded Cabin on the Lake - NOW SLEEPS 10

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

9.4 out of 10, Exceptional, (58)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Central Maine Waterfront

9.6 out of 10, Exceptional, (5)
"This property was full off character with barn wood lined walls and cute fixtures. John was incredibly hospitable and made us feel like family. "
Central Maine Waterfront

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

9.2 out of 10, Wonderful, (23)
"Great view, clean, central a/c, even the ppl using powerboats (4th of July!) were respectful. Exactly the getaway I needed!"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is €202
includes taxes & fees
26 Aug - 27 Aug
Sister A-Frame in Woods B

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

9.8 out of 10, Exceptional, (32)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

ON THE GO!

10.0 out of 10, Exceptional, (1)
"Very clean, owner nearby and responsive to all requests. This is not the Taj Mahal, but it serves it purpose. Will consider again next visit to Hartland."
The price is €133
includes taxes & fees
19 Aug - 20 Aug
ON THE GO!

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

10.0 out of 10, Exceptional, (14)
"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!

Waterfront Lakehouse

9.8 out of 10, Exceptional, (54)
"Wonderful place to stay! Our family loves coming here."
Waterfront Lakehouse

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

9.0 out of 10, Wonderful, (23)
"We had an amazing week. This is the perfect lake cabin… swimming, boating, tubing, campfires at night… we even used a projector to do an outdoor movie night. The owners are very responsive and helpful. We would definitely stay here again."
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

The Modern Maine Retreat

8.8 out of 10, Excellent, (8)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

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."
The price is €174
includes taxes & fees
14 Aug - 15 Aug
Charming cabin in the birches right on the atv trail!

The Great Moose in Stunning Maine Swim, Fish & Kayak

8.0 out of 10, Very good, (4)
"Very basic accommodation. "
The Great Moose in Stunning Maine Swim, Fish & Kayak

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

The Hideout - Just Steps to the Beach!

10.0 out of 10, Exceptional, (9)
"Perfect for relaxing"
The price is €597
includes taxes & fees
21 Aug - 22 Aug
The Hideout - Just Steps to the Beach!

Blake's Cabin

9.6 out of 10, Exceptional, (19)
"Nice place!"
The price is €300
includes taxes & fees
6 Sept - 7 Sept
Blake's Cabin
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

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.