Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Dec 6 - Dec 7
Tomorrow
Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Vacation Rentals in Chester

Property grounds
Cabin on the water!

Cabin in Chester

9.4 out of 10, Exceptional, (27)
"We had a very relaxed, quiet, and comfortable stay!"
United States
Amy D.
Cabin on the water!
Terrace/patio
Rustic cabin in Lincoln Maine

Cabin in Lincoln

1.0 star property
10.0 out of 10, Exceptional, (2)
"This small cabin by the water was a perfect weekend retreat for our family. The rustic feeling of the cabin and the prime location of the property provided a beautiful experience and an easy trip! Inside the cabin is cozy and clean, outside the property offers great water access. We look forward to future stays and adventures spent canoeing on the Penobscot River!"
United States
Nathan B.
$172 nightly
The price is $187
Dec 7 - Dec 8
Total with taxes and fees
Rustic cabin in Lincoln Maine
Interior
Lakefront home with something to enjoy for every season!

Cabin in Lee

9.8 out of 10, Exceptional, (194)
"Very pet friendly, spacious, ample sleeping options"
United States
Jennifer
Lakefront home with something to enjoy for every season!
Interior
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat

Cabin in Millinocket

9.8 out of 10, Exceptional, (30)
"We absolutely loved our stay here. We definitely want to come back. We had just gotten married the week before and we’re looking for some peace and quiet and this was perfect. I love all of the character this place has. It was so comfortable and cozy!"
United States
Amanda F.
Secluded Katahdin View, Lakefront Bliss & Beach Cove Retreat
Property grounds
Lakefront on beautiful Schoodic lake-great fishing and near hiking&ATV trails

Cabin in Brownville

10.0 out of 10, Exceptional, (37)
"Second time staying here. We love it. Plenty of room for 10 of us. Being right on the beautiful lake is amazing. I highly recommend this property. "
United States
Jami B.
Lakefront on beautiful Schoodic lake-great fishing and near hiking&ATV trails
Fridge, microwave, oven, stovetop
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!

Cabin in Brownville

9.4 out of 10, Exceptional, (126)
"Had a great family get away here! Made lots of use of the dock with our boat, as well as kayaking in the cove. Great sunrises and sunsets!"
United States
Marlene D.
Schoodic Escape– NEW FOR 2023 -Whole house generator and FAST Starlink internet!
Property grounds
Log home on untouched cold stream lake

Vacation Home in Lowell

10.0 out of 10, Exceptional, (21)
"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!"
United States
Tori K.
Log home on untouched cold stream lake
Exterior detail
Katahdin Woods & Waters House - close to trails!

Vacation Home in Millinocket

9.8 out of 10, Exceptional, (97)
"Great stay!"
United States
Tina P.
Katahdin Woods & Waters House - close to trails!
Economy Cabin | Terrace/patio
Schlafmans Hollow Solar Cabins

Cabin in Lincoln

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 "
United States
linda
Schlafmans Hollow Solar Cabins
Outdoor dining
Year-Round Lakefront Family Retreat with Private Waterfront and Treehouse

Vacation Home in Lincoln

10.0 out of 10, Exceptional, (5)
"We had the best time at this lake house! The house was spacious, well appointed, and had incredible access to a beautiful lake. I mentioned when we booked that we were staying to celebrate my dad’s birthday and the hosts very kindly left a balloon and other birthday items for us! We had one gorgeous, sunny day that we spent in and out of the lake, and one rainy, cozy day that allowed us to enjoy the enclosed porch and board games. We are already talking about coming back next year because we...
United States
Jan B.
Year-Round Lakefront Family Retreat with Private Waterfront and Treehouse
Property grounds
House close to Mt. Kathadin, Baxter State Park

Vacation Home in East Millinocket

8.6 out of 10, Excellent, (39)
"Perfect family stay. Nice yard to enjoy the outdoors. Very homey andfor a family."
United States
Timothy C.
House close to Mt. Kathadin, Baxter State Park
Fridge, microwave, oven, stovetop
Lake House

Vacation Home in Lincoln

10.0 out of 10, Exceptional, (41)
"Our 2nd time staying here and it was great!!"
United States
Heather M.
Lake House
Fridge, microwave, oven, stovetop
Four Season Getaway on Upper Cold Stream Pond

Vacation Home in Lincoln

10.0 out of 10, Exceptional, (77)
"Wonderful and relaxing lakefront cabin. We always enjoy our stay."
United States
mat c.
Four Season Getaway on Upper Cold Stream Pond
Outdoor dining
Maine Lakeside Retreat

Vacation Home in Lincoln

10.0 out of 10, Exceptional, (38)
"Comfortable and roomy home on a beautiful lake. We spent a wonderful two weeks there. "
United States
Elaine Z.
Maine Lakeside Retreat
Dining
Close to trails! Cozy home base for your snowmobile adventures.

Vacation Home in Millinocket

9.8 out of 10, Exceptional, (11)
"Beautiful house, everything you might need to be comfortable. Near the state park (we went white water rafting there with NEOC), near restaurants, safe, quiet street. Loved this place!"
United States
Susie R.
Close to trails! Cozy home base for your snowmobile adventures.
Interior
Mount Katahdin hideaway!

Apartment in Millinocket

10.0 out of 10, Exceptional, (65)
"Close to everything we needed!"
United States
Andrea C.
Mount Katahdin hideaway!
Property grounds
Very private-modern home -large lake-202ft. of shoreline

Vacation Home in Lakeview Plantation

9.6 out of 10, Exceptional, (29)
"We had a great day! The kids loved the big house and all the different beds they could choose from. Lots of fires were had, fishing, swimming, baseball in the yard. I grew up on Schoodic Lake so it was great to get back there."
United States
Jennifer V.
Very private-modern home -large lake-202ft. of shoreline
Property grounds
Riverside 3 bedroom 2 bath near Baxter State Park

Vacation Home in Millinocket

9.2 out of 10, Wonderful, (66)
"Check-in was a breeze and the kitchen was well-appointed and very clean. Location is spectacular. A canoe and two kayaks were provided and we used them every day. If you want to see bald eagles, this is your place!"
United States
Susan W.
Riverside 3 bedroom 2 bath near Baxter State Park
Interior
South Twin Lake Cabin - Turkey Tail

Cabin in Millinocket

9.0 out of 10, Wonderful, (25)
"The cabin was great for our"
United States
Megan H.
South Twin Lake Cabin - Turkey Tail
Smart TV, DVD player, books
The Loon House is on beautiful, clean spring fed Silver lake.

Vacation Home in Lee

9.8 out of 10, Exceptional, (27)
"Enjoyed our stay very much. House is located on a beautiful spot on Silver Lake with beautiful and spacious lake frontage. We enjoyed hanging out at the picnic table and lounge chairs and using the dock to launch our small aluminum boat and float in the lake! House is spacious and perfect for our family. "
United States
Sharon T.
The Loon House is on beautiful, clean spring fed Silver lake.
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

Maine Lakeside Retreat

Maine Lakeside Retreat

10/10 Excellent
"Was great, clean well equipped and comfortable would do again or recommend "
Gene N. 4-night trip
Posted 5 days ago
Maine Lakeside Retreat

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 $187 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

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 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.