Chester Vacation Rentals

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Vacation Rentals in Chester

Cabin on the water!
Property grounds

Cabin on the water!

9.4 out of 10, Exceptional, (27)
"Had a great long weekend at the cabin, it is beautifully located, and I would stay again in a second "
Cabin on the water!
Schlafmans Hollow Solar Cabins
Economy Cabin | Terrace/patio

Schlafmans Hollow Solar Cabins

2.5 star property
10.0 out of 10, Exceptional, (15)
"schlafman's hollow stay was very pleasant scott the propriator was very nice an' communicative would stay again an' have already recommended to others "
$93 nightly
The price is $102
Oct 2 - Oct 3
Total with taxes and fees
Schlafmans Hollow Solar Cabins
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat
Interior

Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat

9.8 out of 10, Exceptional, (25)
"This was a wonderful getaway for me and my family and perfect place to meet up with family friends."
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat
Mount Katahdin hideaway!
Interior

Mount Katahdin hideaway!

10.0 out of 10, Exceptional, (57)
"Super clean and cozy! Everything provided for a comfortable stay. Walk to the (tiny) downtown, 5 minutes drive to the general store and more, 30 minutes to BSP. Fantastic!"
Mount Katahdin hideaway!
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (126)
"We had a wonderful stay. It was very peaceful. We enjoyed the beautiful setting and kayaking on the lake. Plenty of privacy and excellent views of the lake from inside. Very clean as well. Thank you for a great stay!"
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!
Lakefront home with something to enjoy for every season!
Interior

Lakefront home with something to enjoy for every season!

9.8 out of 10, Exceptional, (185)
"Very pet friendly, spacious, ample sleeping options"
Lakefront home with something to enjoy for every season!
Schoodic Lake House: 2-bedroom, 1 bath, w/ AC
Property grounds

Schoodic Lake House: 2-bedroom, 1 bath, w/ AC

10.0 out of 10, Exceptional, (3)
"Gorgeous location with such a nice home. Host was great!"
Schoodic Lake House: 2-bedroom, 1 bath, w/ AC
Cozy cottage in charming Lincoln, ME with AC
Property grounds

Cozy cottage in charming Lincoln, ME with AC

10.0 out of 10, Exceptional, (4)
"This property was perfectly listed and a wonderful stay! Highly recommend and would stay again! "
Cozy cottage in charming Lincoln, ME with AC
Lake House
Fridge, microwave, oven, stovetop

Lake House

10.0 out of 10, Exceptional, (41)
"We all had a great time. Family vacation coming back "
Lake House
House close to Mt. Kathadin, Baxter State Park
Property grounds

House close to Mt. Kathadin, Baxter State Park

8.6 out of 10, Excellent, (39)
"We were in the area for a weekend long high school basketball tournament. It was located almost in the middle of both the high schools so made it easy to get to the games and back to the house to relax. It was in a nice quiet neighborhood! "
House close to Mt. Kathadin, Baxter State Park
Charming 4-bedroom house in enchanting Millinocket with AC, WiFi
Terrace/patio

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

10.0 out of 10, Exceptional, (7)
"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."
$310 nightly
The price is $338
Oct 14 - Oct 15
Total with taxes and fees
Charming 4-bedroom house in enchanting Millinocket with AC, WiFi
Log home on untouched cold stream lake
Property grounds

Log home on untouched cold stream lake

10.0 out of 10, Exceptional, (20)
"Wonderful time and well appointed cabin with everything you could possibly need for a comfortable stay. The game room was great to get a break from the kids!"
Log home on untouched cold stream lake
Riverside 3 bedroom 2 bath near Baxter State Park
Property grounds

Riverside 3 bedroom 2 bath near Baxter State Park

9.2 out of 10, Wonderful, (65)
"Always a pleasure, could use some seasonal maintenance but overall great!"
Riverside 3 bedroom 2 bath near Baxter State Park
19 Lake St
4 bedrooms, desk, iron/ironing board, WiFi

19 Lake St

10.0 out of 10, Exceptional, (11)
"The property was clean and roomy for a large family. Owner was friendly and accommodating. We greatly appreciated the little touches. We would recommend this property to stay at!"
19 Lake St
Cozy Brownville Cabin: 2 Mi to Schoodic Lake!
House (1 Bedroom) | Interior

Cozy Brownville Cabin: 2 Mi to Schoodic Lake!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Had a great stay at this property, close to the lake, and in walking distance to a restaurant."
Cozy Brownville Cabin: 2 Mi to Schoodic Lake!
Cold Stream Cottage S
Property grounds

Cold Stream Cottage S

10.0 out of 10, Exceptional, (6)
"Clean, cute, cozy, quiet, beautiful water views, truly everything we needed for a nice family weekend! "
Cold Stream Cottage S
Tiny Tiny Caboose Cabin Replica
Property grounds

Tiny Tiny Caboose Cabin Replica

Tiny Tiny Caboose Cabin Replica
Katahdin Woods & Waters House - close to trails!
Exterior detail

Katahdin Woods & Waters House - close to trails!

9.8 out of 10, Exceptional, (96)
"Callie was very helpful with any needs "
Katahdin Woods & Waters House - close to trails!
Maine Lakeside Retreat
Outdoor dining

Maine Lakeside Retreat

10.0 out of 10, Exceptional, (34)
"This house is a great location for fishing both on the ponds and the rivers in the area. We had a great stay and would definitely stay here again."
Maine Lakeside Retreat
Year-Round Lakefront Family Retreat with Private Waterfront and Treehouse
Outdoor dining

Year-Round Lakefront Family Retreat with Private Waterfront and Treehouse

10.0 out of 10, Exceptional, (4)
"Tricia’s property was very clean and comfortable! Location is prime and property was beautiful. "
Year-Round Lakefront Family Retreat with Private Waterfront and Treehouse
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 Chester Hotel Reviews

Schlafmans Hollow Solar Cabins

Schlafmans Hollow Solar Cabins

10/10 Excellent
"It was a get away to a quiet place with a lot of unique features. There is a walking path lit with colorful leds, that was fun to stroll. The out house is funky but very clean, a very rural experience. The cabin was very nice, almost like palacial tree house but on the ground. It was warm enough and I slept well too. This is a get away spot, I recommend, part of which what is not there makes it special. Waldon Pond in a field! I could easly spend a week there doing my writing & a artistic retreat."
John Arthur 5-night trip
Posted 3 days ago
Schlafmans Hollow Solar Cabins

Find out more about Chester

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 Chester 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 Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Lake House: This vacation home rental near Chester is located on a lake and has a balcony, a barbecue grill, and air-conditioning 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 you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

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 Lincoln Memorial Library and Millinocket Memorial Library.

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.