Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chester vacation rentals

Economy Cabin | Terrace/patio

Schlafmans Hollow Solar Cabins

Schlafmans Hollow Solar Cabins
2.5 star property
Lincoln
10.0 out of 10, Exceptional, (16 reviews)
"schlafman's hollow stay was very pleasant scott the propriator was very nice an' communicative would stay again an' have already recommended to others "
United States
linda
The price is ￥14,505
￥15,811 total
includes taxes & fees
Jun 12 - Jun 13
Schlafmans Hollow Solar Cabins
Property grounds

Schlafman's Hollow Solar Cabin 1

Schlafman's Hollow Solar Cabin 1
Lincoln
10.0 out of 10, Exceptional, (1 review)
"Nice and clean. All renewable energy sources. Beautiful area. Peaceful, could do my work and focus."
United States
Terry M.
The price is ￥15,607
￥20,483 total
includes taxes & fees
May 31 - Jun 1
Schlafman's Hollow Solar Cabin 1
Property grounds

Schlafman's Hollow Solar Cabin 2

Schlafman's Hollow Solar Cabin 2
Lincoln
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥15,447
￥20,309 total
includes taxes & fees
May 31 - Jun 1
Schlafman's Hollow Solar Cabin 2
Property grounds

Tiny Tiny Caboose Cabin Replica

Tiny Tiny Caboose Cabin Replica
Lincoln
The price is ￥14,173
￥18,920 total
includes taxes & fees
Jun 6 - Jun 7
Tiny Tiny Caboose Cabin Replica
Private kitchen

New 2026 RV / Mountain View / ATVs

New 2026 RV / Mountain View / ATVs
Lincoln
The price is ￥29,789
￥56,772 total
includes taxes & fees
May 31 - Jun 1
New 2026 RV / Mountain View / ATVs
Fridge, microwave, oven, stovetop

Tranquil lakeside and trailside 5-bedroom house in Lee with gourmet kitchen.

Tranquil lakeside and trailside 5-bedroom house in Lee with gourmet kitchen.
Lee
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay. The lake view was nice, and the three bathrooms were definitely helpful. The neighbors are very close, but it was nice and quiet for the most part. Overall, a very good place to stay for a larger group."
United States
Kenneth W.
The price is ￥45,894
￥100,543 total
includes taxes & fees
May 31 - Jun 1
Tranquil lakeside and trailside 5-bedroom house in Lee with gourmet kitchen.
Property grounds

Rustic cabin in Lincoln Maine

Rustic cabin in Lincoln Maine
Lincoln
10.0 out of 10, Exceptional, (10 reviews)
"Fantastic stay, would come again. "
United States
April T.
The price is ￥23,888
￥29,510 total
includes taxes & fees
Jun 18 - Jun 19
Rustic cabin in Lincoln Maine
Property grounds

Big Narrows Lakeside Cottage

Big Narrows Lakeside Cottage
Lincoln
10.0 out of 10, Exceptional, (1 review)
"If you are looking for a beautiful quiet spot to get away this is it! Very accommodating host, needed something that wasn't in the cabin and host almost immediately brought it over and made sure we had what we needed. Thank you!"
United States
Michael C.
The price is ￥28,665
￥40,271 total
includes taxes & fees
May 31 - Jun 1
Big Narrows Lakeside Cottage
Exterior

Cedar Lake Lodge Millinocket Maine / Lakefront Home

Cedar Lake Lodge Millinocket Maine / Lakefront Home
Long A Township
The price is ￥62,203
￥141,920 total
includes taxes & fees
Jun 1 - Jun 2
Cedar Lake Lodge Millinocket Maine / Lakefront Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Schlafmans Hollow Solar Cabins

Schlafmans Hollow Solar Cabins

10/10 Excellent
"Absolutely loved this place. I would go back every possible chance I could get the owners are super sweet and check in was fast and easy online! He showed us around and told us where everything was super helpful and just overall amazing! If you want a relaxing stay this is the place for you!"
Annabelle 1-night trip
Posted 14 hours ago
Schlafmans Hollow Solar Cabins

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, you can find vacation rentals close to the most popular attractions in Chester, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Chester has to offer?

Charming 4-bedroom house in enchanting Millinocket with AC, WiFi: This vacation home rental near Chester is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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 larger area, you’ll find Millinocket Memorial Library and Jato Highlands Golf Course.

What are vacation rentals like in Chester?

Vacation rentals are privately owned properties you can book for several days or more in Chester. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family gatherings.