Holiday Homes near Main Street, Castine: House Rentals & More

Discover a selection of holiday rentals within easy reach of Main Street that can be your home away from home. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a pool. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Main Street

Showing deals for:26 Sept - 3 Oct

Exceptional

(39 reviews)

Charming cape style beachfront home on Penobscot Bay

Stockton Springs, ME

8% off

NZ$448 per night

includes taxes & fees

Exceptional

(18 reviews)

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Islesboro, ME

8% off

NZ$441 per night

includes taxes & fees

Estate on the sea. The house has been restored to its original "shingled" look.

Exceptional

(58 reviews)

Gorgeous Oceanfront Retreat on Penobscot Bay

Lincolnville, ME

8% off

NZ$2,566 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Main Street

HENRY POINT - Charming Little Cottage on the Shore, Great Kayaking

Sleeps 5 · 3 bedrooms · 1 bathroom

Tranquility on Penobscot Bay Private Retreat: Ask About Discounts Before Booking

Sleeps 7 · 3 bedrooms · 2+ bathrooms

Waterfront stay with scenic deck, grill, smart TVs, shore access - dog-friendly

Sleeps 7 · 3 bedrooms · 2+ bathrooms

Privately owned water view cottage with fabulous views of Penobscot Bay!

Sleeps 4 · 2 bedrooms · 1 bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value