
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.

Rice Farm Hideaway; A little slice of heaven.
This sweet post & beam house is located near town yet private and tucked away in the woods, cozy & comfortable, pet friendly, close to ATV & snowmobile trails, and Baxter State Park, Katadhin Woods and Water, plus numerous lakes and the beautiful Penobscot River. The house can comfortably sleep up to 6 people. The living area is open and sunny with a big kitchen. There is plenty of parking for recreational trailers. Come enjoy a rewarding climb up Katahdin or grab a book and read on the deck.

Lakefront Log Cabin on Pleasant Lake
Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Lakefront Life, Family Friendly
Lakefront Home/Cabin that has an authentic Maine feel. Located on the end of a maintained private dirt road, sitting about 50 ft from the water and nestled in a fairly private cove, this gem is just waiting for you. Enjoy great swimming, fishing, or just lounging on this quiet stocked spring fed lake. all the amenities you need, including washer/dryer. Plenty of parking and a public boat launch close by. Nice swimming area in front of the cabin. 2 BR, one has 2 double beds and the other 1 king.

The Howland Hideout
Welcome to The Howland Hideout! This unique tiny home is the perfect getaway spot for all seasons, filled with the necessary amenities for a comfortable stay and boasting handcrafted touches throughout, you won’t find many places quite like this! Could be a great fit for traveling nurses as there are multiple hospitals nearby. This family friendly location has a large parking area with plenty of room for vehicles/trailers and the patio/backyard are a great place to relax and enjoy the outdoors.

Tranquil lakefront cottage
Right on the water! You will be close to everything when you stay at this centrally-located cozy cottage directly on Mattanawcook Lake with breathtaking views, steps away from boat ramp / dock and park, including beach, basketball courts and playground. One block away to Downtown Lincoln with restaurants and shopping. Relax on the porch or fish from the Private dock (seasonal) /yard. Enjoy family time by the firepit. There is also a rowboat available for use. Off rt 95 / 45 mins from Bangor

28 Holiday Lane Beach Front Cabin
4-Season Cabin next to Morgan's Beach on beautiful Cold Stream Pond rented year round. This is the perfect location for a family vacation or business/working people who travel and have temporary assignments lasting one week to several months. Cabins are fully furnished and include: heat, hot water, electricity, Direct TV, WiFi, trash removal, driveway and roadway plowing. Cabins are 10 minutes to Penobscot Valley Hospital in Lincoln and 40 minutes to EMMC in Bangor. Weekly & Monthly Rates.

Katahdin Riverfront Yurt
Glamping at its best! Beautiful custom built yurt on the banks of the Penobscot river along the Grindstone Scenic Byway. Close to Baxter State Park and majestic Mount Katahdin as well as Katahdin Woods and Waters National Park. Two miles to Penobscot River Trails with miles of groomed cross country skiing and mountain biking. 4 seasons of hiking, biking, fishing, canoeing, kayaking, white water rafting, skiing, and miles and miles of snowmobiling! 1 hour to Bangor 2 hours to Bar Harbor

Elkins Rental
A peaceful place for the family. If you're looking for a quiet out of the way place to stay but still close to all the recreation this area has to offer, this is the place. Baxter state park and Katahdin Woods and waters National Monument close by. ATV trails, Snowsled trails and the Penobscot river all within a couple of miles away . Excellent area for hunting, fishing, hiking, boating and all other 4 season outdoor activities. Plenty of parking area for snowmobile, atv and boats trailers.

Lazy Bear Cabin With River Views!
Welcome to the "Lazy Bear Cabin" across from the beautiful Penobscot River! This 3 bedroom 1 bath home boasts vaulted ceilings with knotty pine on every wall and ceiling. Each bedroom is quite spacious and has closets with lights and ceiling fans. The "master" has a Roku TV. The living room has 2 leather couches, Roku TV. The camp has Spectrum high speed internet with Netflix already set up on the TVs. The kitchen is quite large and will accommodate a large gathering. Washer & Dryer.

Coldstream Private Retreat
Peaceful and private Lakeside Getaway on Cold Stream Pond. Leave your worries behind at this spacious and tranquil lakeside apartment, perfectly perched above the serene waters of Cold Stream Pond. Whether you're here to relax or explore, you’ll love the unbeatable location—just steps from the public boat landing and a short walk to Morgan’s Beach. Sip your morning coffee with stunning water views, spend the day on the lake, and soak in the quiet beauty of Maine’s outdoors.

Private Studio in the Heart of Orono
Slip into the comforts of a private, clean, and modern suite. A plush mattress, crisp white linens, granite countertops, and a rain shower. Walking distance to many of Orono's microbreweries and restaurants. Four minutes to UMaine campus (1 mile), 10 minutes to Bangor, 1 hour and 20 minutes to Acadia National Park/Bar Harbor. *The building next door is undergoing renovations. Guests may hear some light construction noise Mon-Fri during normal working hours.*

Cozy and Quiet Waterfront Cottage in Lincoln Maine
Breathtaking views! Pets welcome! Beautiful private waterfront cabin located on Caribou Pond in Lincoln Maine. Enjoy a peaceful getaway in the great outdoors with all Maine has to offer every season. ATV/Snowmobile trails close by, ice fishing, ski resorts, and so much more. The town of Lincoln with shopping and restaurants is 10 mins away, Bangor is 45 minutes south and Katahdin region is less then an hour north.
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester

Cedar Haven Mission LLC

Home with Sandy Beach On Cambolasse Pond

"The Last Hike" Downtown Millinocket

#1 Schlafman's Hollow Solar Cabins

Bangor Waterfront Area Home. Large 1BR 1.5 Bath

Unique Loft Apartment

Where the best memories are made

Lakefront Log Cabin in Maine Woods
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$29,917 GYD | G$29,917 GYD | G$29,917 GYD | G$34,101 GYD | G$34,101 GYD | G$33,892 GYD | G$39,122 GYD | G$33,683 GYD | G$32,637 GYD | G$29,080 GYD | G$30,126 GYD | G$29,917 GYD |
| Avg. temp | -8°C | -7°C | -1°C | 5°C | 11°C | 16°C | 20°C | 19°C | 14°C | 8°C | 2°C | -4°C |
Frequently Asked Questions
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Chester?
Chester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in Chester have free parking?
Absolutely! We offer over 20 hotel rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have wifi?
Absolutely! We offer over 10 house rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Hotel Rentals in Chester?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do hotel rentals in Chester have air conditioning?
Absolutely! We offer over 20 hotel rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.
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