Chester Holiday Rentals

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Holiday Rentals in Chester

Cabin on the water!

9.4 out of 10, Exceptional, (17)
"Great location to the local trails for ATV riding."
Cabin on the water!

Lakefront home with something to enjoy for every season!

9.8 out of 10, Exceptional, (162)
"James provided my friend and I with the perfect accommodations for a long weekend getaway! Checkin was very easy, the house was clean, and everything was very thoughtful. The kitchen was so well stocked with cookware and all of the small appliances (coffeemaker, toaster oven, air fryer, slow cooker, you name it). The beds were comfortable and there were plenty of towels. We LOVED the quadruple sliding glass doors that let us lounge in the living room but still feel connected to the outdoors!...
Lakefront home with something to enjoy for every season!

Schlafmans Hollow Solar Cabins

3.0 star property
9.8 out of 10, Exceptional, (10)
"Scott was a fantastic host! Everything was clean and comfortable, he was very accommodating and super friendly! Would definitely stay here again!!"
Schlafmans Hollow Solar Cabins

Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!

9.4 out of 10, Exceptional, (113)
"The cabin was perfect for the area. Bein"
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!

Rustic Cabin on Penobscot River (Pet-Friendly!)

9.8 out of 10, Exceptional, (35)
"Awesome water views, quiet and peaceful. I would just mention the steep stairs to loft. Otherwise, very satisfied. Would definitely book again!"
The price is AU$285
includes taxes & fees
26 Nov - 27 Nov
Rustic Cabin on Penobscot River (Pet-Friendly!)

Katahdin Trails Home Base - your cozy home for your Katahdin area adventures!

10.0 out of 10, Exceptional, (19)
"This is an old house that has been renovated and it's so well done! The downstairs is unique and quirky and we loved it. The kitchen has everything you could need. The downstairs bedroom and attached bath/laundry room was perfect for my sister-in-law. (she has trouble navigating stairs) So....for those "seniors" out there I'd like to point out that since this is an old house, the stairs are original and very narrow and steep. All the upstairs bedrooms have double beds so my husband and I...
Katahdin Trails Home Base - your cozy home for your Katahdin area adventures!

Lakefront on beautiful Schoodic lake-great fishing and near hiking&ATV trails

10.0 out of 10, Exceptional, (25)
"Our stay at the Schoodic Lake cabin was absolutely fantastic! The cabin is a real gem—cozy, comfortable, and beautifully situated right by the lake in a very private corner of the shore drive. The location is nothing short of amazing, with breathtaking views and fishing right off the property - good size smallmouth bass visit the shore regularly. We had a wonderfully relaxing week surrounded by nature, and the serene atmosphere of the lake was just what we needed. Emily was incredibly...
Lakefront on beautiful Schoodic lake-great fishing and near hiking&ATV trails

Unique Waterfront Overlooking Mount Katahdin

10.0 out of 10, Exceptional, (50)
"We stayed for a week with my 4 kids (ages 5 - 13) and parents and loved this house! It's a wonderful lake house with everything that you could possibly need. The kitchen is wonderful and the bedrooms were very comfortable. Plenty of room to spread out as well as to convene for meals. The lake is beautiful. "
Unique Waterfront Overlooking Mount Katahdin

Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!

9.8 out of 10, Exceptional, (26)
"It was good. Peaceful"
Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!

Katahdin Woods & Waters House - close to trails!

9.8 out of 10, Exceptional, (84)
"We came for a family wedding in November, so we didn’t get much of a chance to take in all Millinocket has to offer, but loved that guidebooks and trail maps were provided. My husband, father-in-law and two small kids and I were very comfortable in the cozy and clean home. Cooking was easy with everything on-site. Everyone was warm and slept well! Cali made checking in and out a breeze. Wouldn’t hesitate to stay here again when we visit. "
Katahdin Woods & Waters House - close to trails!

Maine Lakeside Retreat

10.0 out of 10, Exceptional, (31)
"We loved our little hideaway!!! It was perfect for our needs & we are definitely talking about next time! "
Maine Lakeside Retreat

House close to Mt. Kathadin, Baxter State Park

8.4 out of 10, Very good, (30)
"Home was just as listed. Perfect size for 3-4 people. Quiet neighborhood, comfortable accomodations close to Baxter State Park. Property manager very gracious and accomodating when I made an error in our departure date. I would definitely stay again."
House close to Mt. Kathadin, Baxter State Park

Large Summer Rental - Near Baxter State Park

9.2 out of 10, Wonderful, (7)
"The place was in good condition and clean. Easy to find and neighborhood seemed quiet."
Large Summer Rental - Near Baxter State Park

Riverside 3 bedroom 2 bath near Baxter State Park

9.4 out of 10, Exceptional, (55)
"LOVED our time there- hiked in Baxter State Park, kayaked down the Penobscot River, roasted s'mores on an open fire....all in one day!!"
Riverside 3 bedroom 2 bath near Baxter State Park

In Town Apartment on Snowmobile/ATV Trail

9.4 out of 10, Exceptional, (3)
"we went to go snowmobiling it was a good time."
In Town Apartment on Snowmobile/ATV Trail

Lakeside Getaway on Upper Coldstream Pond

9.6 out of 10, Exceptional, (12)
"We loved the location of this property. We have our own kayaks and we loved how easy it was to get them in and out of the water. We also enjoyed sitting on the wraparound porch where there is a nice breeze coming off of the other lake across the street. The kitchen is recently renovated and the bedrooms are nice and cozy. I have also never seen a place so well stocked with firewood. Property managers are ver friendly and helpful. 10/10."
Lakeside Getaway on Upper Coldstream Pond

Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat

9.8 out of 10, Exceptional, (16)
"We had a maginificent stay here with my family to celebrate our wedding. The house was stunning as was the location. Our host was fantastic with communication and very easy to work with. It was clean, we had everything we needed and we will definifely be coming back! If i could give 10 stars I would!"
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat

On the road to Baxter Park, and white water rafting rafting.

10.0 out of 10, Exceptional, (4)
"We had a great stay here for marathon weekend. It’s perfect for 2-3 people. Bernie was very helpful, friendly and responsive. Highly recommend checking on Knife Edge brewing up the road for beer + pizza as well."
On the road to Baxter Park, and white water rafting rafting.

Lake House

10.0 out of 10, Exceptional, (35)
"Another awesome company retreat in the mountains of Maine. As always, the house was absolutely fantastic. Everything was clean and in working order. Communication with host was quick and efficient. Thank you so much for letting us use your home we absolutely love it. Hope to be back again next year."
Lake House

Very private-modern home -large lake-202ft. of shoreline

9.8 out of 10, Exceptional, (27)
"Plenty of room for everyone, quiet location and beautiful views of the lake "
Very private-modern home -large lake-202ft. of shoreline
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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Other types of properties in Chester you may be interested in

Cabin on the water!

9.4 out of 10, Exceptional, (17)
"Great location to the local trails for ATV riding."
Cabin on the water!

Gateway Inn

2.5 star property
8.4 out of 10, Very good, (353)
"Right in a location where I needed a motel."
The price is AU$168
includes taxes & fees
26 Nov - 27 Nov
Gateway Inn

Katahdin Inn & Suites

2.0 star property
8.0 out of 10, Very good, (119)
"The building doesn’t look like a hotel. The sign was not well lit. They are doing renovations which look like they will be nice. Breakfast was underwhelming. The room was clean and large. Be careful when heading out of town towards Greenville, GPS may send you to a dirt road that is private property."
The price is AU$230
includes taxes & fees
26 Nov - 27 Nov
Katahdin Inn & Suites
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester has to offer?

Katahdin Trails Home Base - your cozy home for your Katahdin area adventures!: This holiday home rental outside of Chester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Chester?

Explore the area and family-friendly sights such as Mt. Jefferson, or get out into nature at a spot like Penobscot River. In the wider area, you’ll find Lincoln Memorial Library and Jato Highlands Golf Course.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.