Blue Shutter
2 Bedrooms | 2 Beds | 1 Bath | 4 Guests
**EXCLUSIVE BEACH ACCESS** A sun-drenched two-bedroom cottage with its own stairway to an exclusive beach, boasting unobstructed views of Casco Bay, Diamond Pass, and the Portland skyline from virtually every room and the spacious patio. Thoughtfully appointed inside with a breakfast bar, comfy living area, and fully equipped kitchen—and outside with a Weber grill, dining for six under an oversized umbrella, and an outdoor shower to rinse off the sand. Available for weekly Sunday-to-Sunday stays beginning August 3, 2025—your private Peaks Island retreat.
from
$3000 per week
Use code SHUDDER for 10% off August!
Gorges Sunset Two
WATER VIEW CONDO 2 Bedrooms | 3 Beds | 1 Bath | 4 Guests
A sleek, brand-new two-bedroom, one-bath condo on Peaks Island’s main street—just a five-minute stroll to the ferry, market, ice cream, restaurants, and beach. Enjoy unobstructed Casco Bay views from your private, expansive deck. Inside, find an open-concept kitchen/dining/living area, pristine new bathroom, in-unit laundry, dishwasher, and smart TV—all bathed in natural light. Bedrooms include one queen and two twins, making it perfect for couples or small families. Sleeps 4; available nightly (3-night minimum), weekly, and monthly.
from
$250/night
Use code GORGES for -20% Aug & Sep!
Gorges Sunset One
WATER VIEW CONDO 2 Bedrooms | 3 Beds | 1 Bath | 4 Guests
A brand-new two-bedroom, one-bath condo on Peaks Island’s main street—just a five-minute stroll to the ferry, market, ice cream shop, restaurants, and beach. Enjoy sweeping Casco Bay views from your private, expansive deck. Inside, an open-plan kitchen/dining/living area, sleek new bathroom, in-unit laundry, dishwasher, and smart TV offer effortless comfort. Bright, airy bedrooms (one queen, two twins) make it ideal for weekend getaways or longer stays. Sleeps 4; nightly, weekly, and monthly rentals available.
from
$225/night
Use code GORGES for -20% Aug & Sep!
Reed's View
4 Bedrooms | 5 Beds | 1 Bath | 8 Guests
A lovingly restored 100-year-old seaside cottage just steps from the water on a quiet, dead-end road—perfect for a peaceful family retreat. Enjoy uninterrupted views of Josiah’s Cove “all the way to Portugal,” modern comforts (wireless internet, new appliances, skylights, plush mattresses), and salt-air mornings on the front porch. Sleeps up to 8; no pets, smoking, or events. Take advantage of nearby beaches, bike paths, tennis courts, kayaking, fishing off the rocks, and rinse off in your private outdoor shower.
from
$500/night | $3500/week
Prince's View
4 Bedrooms | 5 Beds | 2 Baths | 8 Guests
A sentimental family cottage perched high above Josiah’s Cove on a quiet, dead-end road—perfect for a peaceful getaway. Colorfully decorated with cherished heirlooms and freshly updated (new insulation, windows, floors, full bath, laundry), it features a wrap-around porch with ocean glimpses, a secluded outdoor shower, and a short stroll through “The Magic Woods” to the shore. Sleeps up to 8; no pets, smoking, or parties; linens available to rent.
from
$500/night | $3500/week
AnaCarlos
3 Bedrooms | 5 Beds | 1 Bath | 5 Guests
Sitting high on a hill, this perfectly charming cottage is private and cozy. Sunroom, covered porch, and ocean views. A quaint cottage fully embracing the idea that big things can happen in small spaces. Unwinding to be had all around. There is no laundry at this home. WiFi, TV, view, kitchen, clawfoot tub, single floor living space. Dogs allowed.
$1300 per week
Sunset View
3 Bedrooms | 3 Beds | 1 Bath | 5 Guests
A rustic three-bedroom, one-bath bayside cottage on a quiet private road across from the beach, offering million-dollar views of Casco Bay and Diamond Pass from its covered front porch. Inside, unwind in the cozy living area (with a sofa that converts to a twin bed), whip up meals in the spacious propane-stove kitchen, and freshen up in the stand-up shower. Outside, fire up the grill and soak in the scenery. No WiFi or dishwasher—true unplugged relaxation.
$1595 per week
Whale of a Time
3 Bedrooms | 3 Beds | 1 Bath | 6 Guests
A bright, sunny three-bedroom cottage (queen + two full beds) just a short walk to the ferry, shops, and three local beaches. Southern exposure fills the front deck and cozy indoor porch with light, while the spacious backyard invites lawn games. Inside, you’ll find a full kitchen (gas stove, lobster pot), Wi-Fi, smart TV, beach chairs, grill, and washer/dryer.
$1750 per week
The Dwelling Place
2 Bedrooms | 3 Beds | 1 Bath | 6 Guests
A charming single-level Peaks Island cottage tucked off Main Street, featuring two bedrooms (queen + full), a futon, vaulted ceilings, and French doors opening to a patio with grill. Outside, enjoy a large fenced yard, fire pit, covered front porch, bikes, kayaks, and A/C—just a 6-minute walk to the ferry, restaurants, and market. Sleeps 6; no pets; Sunday-to-Sunday rentals through Labor Day (weekend stays by inquiry through October).
from
$1600 per week
Home of Cottage
3 Bedrooms | 4 Beds | 2 Baths | 6 Guests
A quintessential Maine cottage on Peaks Island, showcasing beadboard walls, custom exterior woodwork, and a welcoming wrap-around porch with a hammock. Inside are three sunlit bedrooms (queen, full, and two twins) sharing a Jack & Jill bath, plus a fully stocked kitchen and cozy living spaces. Outside, enjoy a covered porch for dining, an outdoor shower, and a grill. Just a short stroll or 10-minute bike ride to beaches, shops, galleries, and the ferry—perfect island living for up to 6 guests.
from
$557/night