Holiday Rentals in Chester

April 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

May 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday
    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Chester

Cabin on the water!

9.4 out of 10, Exceptional, (19)
"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, (176)
"We so enjoyed the cabin and hope to be back in the near future!"
Lakefront home with something to enjoy for every season!

Charming 4-bedroom house in enchanting Millinocket with AC, WiFi

10.0 out of 10, Exceptional, (1)
"It was a hreat stay. From the booking on, great communication woth the host. Beds were extremely comfortable. Plenty of space for all of us."
Charming 4-bedroom house in enchanting Millinocket with AC, WiFi

Katahdin Woods & Waters House - close to trails!

9.8 out of 10, Exceptional, (87)
"We had a greay stay. The house was clean, tidy, and in a great location. "
Katahdin Woods & Waters House - close to trails!

Rustic Cabin on Penobscot River (Pet-Friendly!)

9.8 out of 10, Exceptional, (37)
"Would stay again, nice host, beautiful river view, really enjoyed the stay, enjoyed poking around in quaint town-especially Renys department store. Can’t wait to go back for a bonfire and kayak or canoeing, barbecuing on the porch grill. Sweet!"
The price is €165
includes taxes & fees
9 May - 10 May
Rustic Cabin on Penobscot River (Pet-Friendly!)

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

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

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

9.4 out of 10, Exceptional, (116)
"The setting and house is lovely. Lake is beautiful. "
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!

South Twin Place - Comfortable year-round home on the shores of South Twin Lake!

10.0 out of 10, Exceptional, (8)
"Can't go wrong staying here! The hosts are very nice and accomodating, and the place is just great overall. "
South Twin Place - Comfortable year-round home on the shores of South Twin Lake!

Mount Katahdin hideaway!

10.0 out of 10, Exceptional, (44)
"Elizabeth's place was in a nice location for visiting Millinocket."
Mount Katahdin hideaway!

Riverside 3 bedroom 2 bath near Baxter State Park

9.4 out of 10, Exceptional, (57)
"Gorgeous location along the River! Peaceful and exactly what we were looking for."
Riverside 3 bedroom 2 bath near Baxter State Park

Close to trails! Cozy home base for your snowmobile adventures.

9.6 out of 10, Exceptional, (5)
"The house was clean and as described. The property manager was great. She greeted us upon arrival and showed us everything we needed to know around the house. I would recommend this rental and we would stay here again. "
Close to trails! Cozy home base for your snowmobile adventures.

Katahdin Comfort - A Beautiful Four Bedroom Home

10.0 out of 10, Exceptional, (41)
"I would recommend very nice place"
Katahdin Comfort - A Beautiful Four Bedroom Home

Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat

9.8 out of 10, Exceptional, (16)
"Great privacy and lovely cabin on the lake!"
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat

Cold Stream Cottage S

Cold Stream Cottage S

Luxurious and very private lake front cottage

Luxurious and very private lake front cottage

The Loon House is on beautiful, clean spring fed Silver lake.

10.0 out of 10, Exceptional, (22)
"We loved our week at the Loon House. The camp is clean and comfortable. Lake is clear and sandy bottom is easy on the feet. Owners are responsive and the camp is well stocked. Will be booking again for next year."
The Loon House is on beautiful, clean spring fed Silver lake.

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

10.0 out of 10, Exceptional, (32)
"Cabin was very nice and the close proximity to the lake was great. Would stay again."
Lakefront on beautiful Schoodic lake-great fishing and near hiking&ATV trails

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

10.0 out of 10, Exceptional, (21)
"The house is so cozy and welcoming! "
Katahdin Trails Home Base - your cozy home for your Katahdin area adventures!

Large Summer Rental - Near Baxter State Park

9.2 out of 10, Wonderful, (7)
"Lots of space and easy to get to Millinocket Lake and Baxter"
Large Summer Rental - Near Baxter State Park

Schlafmans Hollow Solar Cabins

3.0 star property
10.0 out of 10, Exceptional, (11)
"Great all around, real nice owner"
The price is €78
includes taxes & fees
11 May - 12 May
Schlafmans Hollow Solar Cabins
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chester you may be interested in

Cabin on the water!

9.4 out of 10, Exceptional, (19)
"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, (365)
"Great service clean property. Definitely, stay again."
The price is €96
includes taxes & fees
1 May - 2 May
Gateway Inn

Katahdin Inn & Suites

2.0 star property
8.2 out of 10, Very good, (134)
"The staff was AMAZING!!! The other stuff was minor like no hand soap in the bathroom in our room. "
The price is €97
includes taxes & fees
1 May - 2 May
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.

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?

Charming 4-bedroom house in enchanting Millinocket with AC, WiFi: 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.