Chester Vacation Rentals from $97: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chester vacation rentals

1. Schlafmans Hollow Solar Cabins

Lincoln

Susan

$89 nightly

Sep 3 - Sep 4

Total with taxes and fees

2. Schlafman's Hollow Solar Camp Cabin 1

Lincoln

Terry M.

$109 nightly

Sep 1 - Sep 2

Total with taxes and fees

3. Schlafman's Hollow Solar Camp Cabin 2

Lincoln

$109 nightly

Sep 1 - Sep 2

Total with taxes and fees

4. Rustic cabin in Lincoln Maine

Lincoln

Amy

$172 nightly

Sep 1 - Sep 2

Total with taxes and fees

Coffee/tea maker, fridge, microwave, stovetop

5. New 2026 RV / Mountain View / ATVs

Lincoln

$359 nightly

Sep 1 - Sep 2

Total with taxes and fees

6. Book your stay to find out why this Maine “camp” is a generational favorite!

Lee

$346 nightly

Sep 28 - Sep 29

Total with taxes and fees

7. Camo Dome Tent

Lincoln

$245 nightly

Sep 2 - Sep 3

Total with taxes and fees

8. Big Narrows Lakeside Cottage

Lincoln

Michael C.

$235 nightly

Sep 2 - Sep 3

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

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

Baxter Park Inn

8/10 Good

"Owners live on site. Room spacious and has everything. I didn’t explore the building amenities, but there is a breakfast room with a few packaged breakfast items. The building is worn and drab, but clean. There is no elevator but there are rooms on the first floor."

Schoodic Escape

10/10 Excellent

"We had a great stay here! This is a lovely cabin in a little neighborhood, but still feels private. We brought our canoe and kayaks and were on the water a lot. Entry is very shallow and kid friendly. Our kiddo caught his first fish right off the dock! Bathrooms, kitchen, bedrooms were very clean. Common areas a bit less so. This cabin feels like staying at a friends house. There is a Trade Winds/Hannaford grocery store about 15 mins away in Milo — we brought all our food but could have saved space and just shopped there. There’s a lovely heated mudroom — excellent for winter, but in the summer a laundry drying rack or hooks in the bathroom would have been helpful for drying swimsuits and towels. The cabin was comfortable temperature wise, but fans in the bedrooms would have been welcome as well. Kitchen is incredibly well stocked with pots, pans, utensils. Many chairs on the deck, along with a picnic table. Overall, really fantastic. We’d absolutely go back."

1-bedroom off grid cabin in serene Woodville perfect for relaxing getaway

10/10 Excellent

"I don't even know where to start, from the first day until the last it was just so quiet and peaceful. Charles was so nice and extremely helpful. We felt at home there. The fishing was absolutely amazing as was the the wildlife and the scenery. We love how it's off the grid and a few miles in on a dirt road (which just adds to the lore of this hidden gem) We fully recommend this to anyone who just needs to decompress from normal everyday life and relax. We definitely will be coming back, our kids loved it and we did to! We have absolutely no complaints and if I could I would give it ten stars! Thank you Charles and your family for allowing us to enjoy the beauty hat you have! Sincerely The Brancaccios"

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 $97 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.

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?

5-Bedroom Lakefront Retreat, Sandy Beach & Direct Mt. Katahdin Views, South Twin: This vacation home rental near Chester is on a lake and equipped with 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 Mattanawcook Pond.

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.

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chester vacation rentals

1. Schlafmans Hollow Solar Cabins

2. Schlafman's Hollow Solar Camp Cabin 1

3. Schlafman's Hollow Solar Camp Cabin 2

4. Rustic cabin in Lincoln Maine

5. New 2026 RV / Mountain View / ATVs

6. Book your stay to find out why this Maine “camp” is a generational favorite!

7. Camo Dome Tent

8. Big Narrows Lakeside Cottage

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

10. Cedar Lake Lodge Millinocket Maine / Lakefront Home

11. 3-bedroom house in tranquil Millinocket

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Baxter Park Inn

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

Briarwood Motor Inn

Schoodic Escape

Quaint 1 Bedroom + Loft/1 Bath streamside Timber Frame cabin near Lincoln, ME.

The Whitetail and Suites

House close to Mt. Kathadin, Baxter State Park

Pamola Motor Lodge

1-bedroom off grid cabin in serene Woodville perfect for relaxing getaway

Find out more about Chester

Frequently asked questions

Go further with the Expedia app