Entire home

Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches

Family-friendly holiday home in Long Island

Chestnut Hill Inn and Retreat Center on Long Island Maine is a haven for relaxation. Unwind in the wrap-around porches, enjoy family time around the firepit, or indulge in books and games from the library. With its commercial kitchen and multiple dining areas, this retreat center is perfect for gatherings big or small.

Exceptional

Entire home

7 bedrooms6 bathroomsSleeps 14466 sq m

Popular amenities

Dryer
Washer
Barbecue grill
Fireplace
Kitchen
Parking available

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches

Spacious, Comfort-Filled Accommodations
7 beautifully appointed bedrooms, 4 with private ensuites, plus a versatile bonus room with futon—sleep up to 16 guests in total.

Inviting living areas including a TV-equipped lounge, dual dining rooms, a cozy library nook, and peaceful sitting spots sprinkled throughout.

Gourmet-Ready Commercial Kitchen
Fully stocked with two fridge/freezers, all major and small appliances, pots, pans, platters, serving ware—everything you need to create island feasts.

Ample prep space and two separate dining areas make group meals a breeze.

Endless Indoor Entertainment
A library brimming with books, puzzles, and games for every age.

Poker table with chips—host your own tournament!

Board games, card decks, and comfy reading chairs for laid-back afternoons.

Dreamy Outdoor Living
Wrap-around porches on two sides: sip your morning coffee as waves crash, or lounge with a sunset cocktail.

Front porch overlooks the easy path to Main Beach—perfect for people-watching or catching the evening light.

Screened porch with TV for bug-free movie nights.

Firepit oasis with seating for eight—roast marshmallows under the stars.

Outdoor shed stocked with island bikes, beach chairs, and sand toys—just help yourself!

Unbeatable Island Location
A 3-minute stroll to two of Maine’s finest sandy beaches.

Just ¾ mile from the historic Pier & general store.

Only ½ mile to The Bakehouse’s scrumptious grab-and-go gourmet offerings.

Explore rocky coves, tide pools, and miles of shoreline—adventure awaits!

Perfect For…
Family reunions | Corporate retreats | Girls’ wine-down weekends | Father-son fishing trips | Summer vacations

Create lasting memories in a home that’s as grand as your guest list. Book your unforgettable Maine island getaway today!

Note: Owners’ quarters are discreetly located at the back of the inn. We’re on-island only occasionally, with two outdoor cameras for peace of mind.

Property amenities

Beach

Beach loungers
Beach towels

Internet

Available in the house: Free WiFi

Parking and transport

Parking on site

Kitchen

Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Kitchenette
Lobster/crab pot
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster

Dining

Dining table

Bedrooms

7 bedrooms
Bedsheets provided

Bathroom

5.5 bathrooms
Bathtub or shower
Hair dryer
Soap
Toilet paper
Towels provided

Living spaces

Dining table
Fireplace
Living room
Separate dining area

Entertainment

Books
DVD player
Games
Smart TV
Stereo
Video library

Outdoor areas

Balcony
Barbecue grill
Firepit
Garden
Outdoor furniture

Laundry

Laundry facilities
Washing machine

Work spaces

Printer

Comfort

Heating

Pets

Pet friendly
Welcoming dogs only
Up to 23 kg per pet

Suitability/Accessibility

Designated smoking areas

Services and conveniences

Iron/ironing board

Things to do

Bicycles
Pickleball
Tennis
Basketball nearby
Birdwatching nearby
Fishing nearby
Kayaking nearby
Motor boating nearby
Sailing nearby
Swimming nearby
Windsurfing nearby

Safety features

Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock

General

At least 10% of profits reinvested in community and sustainability
Bicycles
Comprehensive recycling policy
Garden
Humane treatment of captive wild animals
Local artist showcase
Reusable coffee/tea filters
Unit size: 5,019 square feet

Similar properties

Fridge, oven, stovetop, coffee/tea maker

Kitchen
Washer
Dryer
Free WiFi

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in and check-out are available

Minimum check-in age - 30

Check-out

Check-out before 10:00 AM

Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets are allowed

Service animals are welcome, and are exempt from fees

Welcoming dogs only

1 total (up to 23 kg per pet)

Note from host: All Pets need to be preapproved prior to booking.

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings, birthday parties, weddings

Events need to be preapproved prior to booking.

Smoking

Smoking allowed: in designated areas

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 14

Note from host: Events need to be preapproved prior to booking.

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Long Island is home to this holiday home. Casco Bay Lines Ferry Terminal and Bayside Bowl are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Maine Narrow Gauge Railroad Company and Museum and Portland Observatory. Travelling with kids? Consider Southworth Planetarium, or check out an event or a game at Merrill Auditorium. With kayaking, windsurfing and power boating nearby, you'll find plenty of adventures in the water.

Visit our Long Island travel guide

View more Holiday homes in Long Island

Long Island, ME

What's nearby

Sand Beach - 33 min drive - 6.6 km
Casco Bay Lines Ferry Terminal - 53 min drive - 10.2 km
Cross Insurance Arena - 54 min drive - 10.6 km
State Theatre - 55 min drive - 11.3 km
East End Beach - 55 min drive - 11.7 km

Getting around

Portland Transportation Center - 60 min drive
Portland, ME (PWM-Portland Intl. Jetport) - 68 min drive

Restaurants

‪North43Bistro - ‬72 min drive
‪McDonald's - ‬73 min drive
‪Dunkin' - ‬74 min drive
‪Double Great Coffee - ‬68 min drive
‪Dockside Grill - ‬76 min drive

Frequently asked questions

Is Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches?

Check-in begins at 4:00 PM.

What time is check-out at Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches?

Checkout is at 10:00 AM.

Where is Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches located?

Located in Long Island, this family-friendly holiday home is steps from Casco Bay and within 6 mi (10 km) of Sand Beach and Little Diamond Island. Maine Narrow Gauge Railroad Company and Museum and Portland Observatory are also within 9 miles (15 km).