Chester Vacation Rentals

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Vacation Rentals in Chester

Cabin on the water!
9.2 out of 10, Wonderful, (15)
"Loved the location. We will try and stay again at some point."
Cabin on the water!
Mount Katahdin hideaway!
10.0 out of 10, Exceptional, (15)
"Apartment was as described. Everything was Clean and the Kitchen had everything you need if you want to cook. The location was ideal for us being walking distance to both town and the dog park. Elizabeth was very easy to deal with and she had drinks and fruit and other nice things in the fridge waiting for us on arrival. The Roku and Wifi all worked perfectly. If we are ever in Millinocket again we would definitely stay here. Thanks Elizabeth for everything."
Mount Katahdin hideaway!
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!
9.4 out of 10, Exceptional, (103)
"If you are planning a stay for more than a couple days - there is no clothes washer or dryer."
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!
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Rustic Cabin on Penobscot River (Pet-Friendly!)
9.8 out of 10, Exceptional, (27)
"We have stayed here before and always like it. Clean and comfortable. The host is a great & friendly guy. This is so close to town and to our family. We will stay again for sure! TY"
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, (8)
"House was quite nice and clean. Checkin was quite accommodating as we were arriving late. Great recommendations for dinner."
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, (21)
"Beautiful spot on the lake, very private. Stayed with family to view the solar eclipse and it was perfect. Plenty of room - and fully stocked kitchen (pots, pans, spices, etc.) and bathroom to make it easy to just arrive (best to arrive with groceries though - it takes awhile to get back to any shops!). Bald eagles (and a golden eagle sighting) were quite a bonus."
Lakefront on beautiful Schoodic lake-great fishing and near hiking&ATV trails
Lakefront home with something to enjoy for every season!
9.6 out of 10, Exceptional, (151)
"Really well stocked house right on the lake (and dog friendly!). Neighbors weren’t too close and the fishing was A+. If it wasn’t already booked I’d try to grab another weekend this summer - two nights wasn’t enough!"
Lakefront home with something to enjoy for every season!
Unique Waterfront Overlooking Mount Katahdin
10.0 out of 10, Exceptional, (49)
"This was our second stay at this magical property! We were there for a long weekend with adult kids and one high schooler. Everyone had had a bit of a stressful Fall and the home in its gorgeous was the cure for what ailed us. Gorgeous, super fun, creatively designed house with some of the best views I've seen anywhere, even on gray days. Convenient to lots of great hiking and mountain biking as well as kayaking/canoeing and (for the hardier souls) swimming. Highly recommend!"
Unique Waterfront Overlooking Mount Katahdin
Maine Lakeside Retreat
10.0 out of 10, Exceptional, (25)
"This house on lake has everything you need to enjoy a family getaway. We absolutely loved everything there and being close to town"
Maine Lakeside Retreat
Katahdin Woods & Waters House - close to trails!
9.8 out of 10, Exceptional, (76)
"My wife and I really enjoyed our stay at your house. We found it very comfortable and relaxing. The amenities were perfect and will recommend your VRBO to our friends."
Katahdin Woods & Waters House - close to trails!
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat
9.8 out of 10, Exceptional, (9)
"Nice cabin for seclusion and quick enough access to Baxter State Park. Note this is a half bath house not full…only shower is outside so be prepared for that. Beautiful view of lake and Mt Katahdin. Beach area made for easy access of water on kayaks and canoes."
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat
Riverside 3 bedroom 2 bath near Baxter State Park
9.4 out of 10, Exceptional, (47)
"This was the best vacation our family had in a long time. It’s private, and spacious, and close to town but right on the water. We would stay again for sure."
Riverside 3 bedroom 2 bath near Baxter State Park
Lake Side Cottage, Central Maine, Private dock, Great Sunsets. Very Calming.
9.4 out of 10, Exceptional, (16)
"Quiet and relaxing"
Lake Side Cottage, Central Maine, Private dock, Great Sunsets. Very Calming.
Lakeside Getaway on Upper Cold Stream Pond (Little Narrows)
9.8 out of 10, Exceptional, (9)
"Great place to stay if your looking for a lake experience. Clean and plenty of room. Beds are super comfy. This is our 3rd year here and will be back."
Lakeside Getaway on Upper Cold Stream Pond (Little Narrows)
Lake House
10.0 out of 10, Exceptional, (29)
"had a great time enjoyed the fire pit. the town of lincoln had everything we needed,also enjoy the many lakes to fish in around the area."
Lake House
Very private-modern home -large lake-202ft. of shoreline
9.6 out of 10, Exceptional, (25)
"Our family of five enjoyed a fun filled week at Tony's private cove on beautiful Schoodic Lake. We canoed, swam, played endless board games that were at the camp, cooked delicious meals on the grill provided and ended each day with a relaxing camp fire that looked out over the lake. There were plenty of sleeping and hang out spots for everyone, but I enjoyed the screened in porch the most- watching the hummingbirds while drinking coffee. Thank you Tony for sharing your place with our family!"
Very private-modern home -large lake-202ft. of shoreline
South Twin Lake Cabin - Turkey Tail
8.4 out of 10, Very good, (15)
"3 days and nights great cabin friends attentive host. Would highly recommend"
South Twin Lake Cabin - Turkey Tail
Snowmobiling, hiking, rafting paradise from this gorgeous Millinocket home
10.0 out of 10, Exceptional, (13)
"As soon as I saw the enclosed porch I knew it would be perfect. And the rest of the house was wonderful too, warm, clean, comfortable. This was our 1st trip to northern Maine. Here for the solar eclipse. And we will be back to this beautiful home away from home."
Snowmobiling, hiking, rafting paradise from this gorgeous Millinocket home
New YURT on the bank of the Penobscot river. Near Baxter & National monument
10.0 out of 10, Exceptional, (4)
"Honestly didn't know what to expect from a Yurt. This property is in a beautiful location right next to the river. It is all new, extremely clean and comfortable. I would highly recommend this to anyone wanting to stay in this area."
The price is CA $308
CA $512 total
includes taxes & fees
Jul 17 - Jul 18
New YURT on the bank of the Penobscot river. Near Baxter & National monument
Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!
9.8 out of 10, Exceptional, (18)
"My husband dog and I, very much enjoyed the camp. So peaceful. We ended up getting up there later than planned. John waited for us. He was so kind and helpful. My car ended up having issues and needed to be fixed. I texted John. He sent me to a garage in Lincoln. They were so nice. The lake is clean and clear. So beautiful. I enjoyed fishing while my husband relaxed in the lake. John also told us about some good fishing and walking places. The camp has all you need for cooking and eating....
Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!
Don't see what you're looking for?
See all available properties in Chester
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.

Other types of properties in Chester you may be interested in

Cabin on the water!
9.2 out of 10, Wonderful, (15)
"Loved the location. We will try and stay again at some point."
Cabin on the water!
Katahdin Inn & Suites
2.0 star property
8.4 out of 10, Very good, (57)
"Little work being done while there wasn’t bad just ruined some the aesthetics "
The price is CA $219
CA $239 total
includes taxes & fees
Jun 23 - Jun 24
Katahdin Inn & Suites
Gateway Inn
2.5 star property
8.2 out of 10, Very good, (286)
"Great place to stay. Nothing overly fancy but very recieving. Super nice staff."
The price is CA $137
CA $149 total
includes taxes & fees
Jun 22 - Jun 23
Gateway Inn
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester vacation rentals we have selected for you start as low as CA $308 per night. Entering your travel dates in the search wizard 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. 

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?

Katahdin Trails Home Base - your cozy home for your Katahdin area adventures!: This vacation home rental near 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 larger area, you’ll find Lincoln 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.

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