Holiday rentals near Main Street
We found 208 holiday rentals — enter your dates for availability
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:14 Nov - 21 Nov
Image gallery for Charming Cottage in Quaint Coastal Bayside, Maine with Waterview
1010 out of 10 rating
Exceptional
(14 reviews)
Charming Cottage in Quaint Coastal Bayside, Maine with Waterview
Lincolnville, ME
15% off
Price is S$2,856
S$2,856
S$408 per night
includes taxes & fees
Image gallery for Rustic Maine Cottages with glorious water view, path to our shoreline
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Rustic Maine Cottages with glorious water view, path to our shoreline
Castine, ME
5% off
Price is S$2,522
S$2,522
S$360 per night
includes taxes & fees
Image gallery for Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
1010 out of 10 rating
Exceptional
(18 reviews)
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
Islesboro, ME
8% off
Price is S$2,327
S$2,327
S$332 per night
includes taxes & fees
Image gallery for Unique, Charming Cottage on Penobscot Bay - Gorgeous Views!
1010 out of 10 rating
Exceptional
(8 reviews)
Unique, Charming Cottage on Penobscot Bay - Gorgeous Views!
Lincolnville, ME
8% off
Price is S$5,322
S$5,322
S$760 per night
includes taxes & fees
Image gallery for The Best of Maine: Waterfront home/private beach on Penobscot!
1010 out of 10 rating
Exceptional
(9 reviews)
The Best of Maine: Waterfront home/private beach on Penobscot!
Stockton Springs, ME
8% off
Price is S$3,625
S$3,625
S$518 per night
includes taxes & fees
Image gallery for Sun, salt and sand @ Heart Rock House! Private beach/8 min drive to Belfast!
1010 out of 10 rating
Exceptional
(25 reviews)
Sun, salt and sand @ Heart Rock House! Private beach/8 min drive to Belfast!
Searsport, ME
8% off
Price is S$3,553
S$3,553
S$508 per night
includes taxes & fees
Image gallery for Charming Coastal Maine Cottage Overlooking Penobscot Bay!
1010 out of 10 rating
Exceptional
(13 reviews)
Charming Coastal Maine Cottage Overlooking Penobscot Bay!
Stockton Springs, ME
8% off
Price is S$3,088
S$3,088
S$441 per night
includes taxes & fees
Image gallery for Gorgeous estate overlooking Penobscot Bay
9.89.8 out of 10 rating
Exceptional
(63 reviews)
Gorgeous estate overlooking Penobscot Bay
Lincolnville, ME
8% off
Price is S$14,470
S$14,470
S$2,067 per night
includes taxes & fees
Image gallery for Peaceful location perfect for couples or small family
9.89.8 out of 10 rating
Exceptional
(88 reviews)
Peaceful location perfect for couples or small family
Brooksville, ME
15% off
Price is S$2,001
S$2,001
S$286 per night
includes taxes & fees
Image gallery for Sweet cottage on Cape Rosier
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Sweet cottage on Cape Rosier
Harborside, ME
7% off
Price is S$1,345
S$1,345
S$192 per night
includes taxes & fees
Image gallery for Secluded Oceanfront with Private Beach & Island
1010 out of 10 rating
Exceptional
(41 reviews)
Secluded Oceanfront with Private Beach & Island
Stockton Springs, ME
8% off
Price is S$3,949
S$3,949
S$564 per night
includes taxes & fees
Image gallery for Gorgeous Waterfront Estate In Historic Bayside
1010 out of 10 rating
Exceptional
(69 reviews)
Gorgeous Waterfront Estate In Historic Bayside
Lincolnville, ME
8% off
Price is S$15,679
S$15,679
S$2,240 per night
includes taxes & fees
Image gallery for Country Mama's Modern Artsy Cottage
1010 out of 10 rating
Exceptional
(6 reviews)
Country Mama's Modern Artsy Cottage
Sedgwick, ME
12% off
Price is S$3,476
S$3,476
S$497 per night
includes taxes & fees
Image gallery for Comfortable & Charming 2-bedroom barn in peaceful Brooksville with Waterfront
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Comfortable & Charming 2-bedroom barn in peaceful Brooksville with Waterfront
Brooksville, ME
15% off
Price is S$1,901
S$1,901
S$272 per night
includes taxes & fees
Image gallery for Island log home in Maine with ocean views
1010 out of 10 rating
Exceptional
(79 reviews)
Island log home in Maine with ocean views
Islesboro, ME
8% off
Price is S$1,618
S$1,618
S$231 per night
includes taxes & fees
Image gallery for Peaceful waterfront home on quiet cove with outdoor sauna near shops & hiking
8.88.8 out of 10 rating
Excellent
(8 reviews)
Peaceful waterfront home on quiet cove with outdoor sauna near shops & hiking
Stockton Springs, ME
8% off
Price is S$3,609
S$3,609
S$516 per night
includes taxes & fees
Image gallery for Midcoast Forest Getaway
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Midcoast Forest Getaway
Searsport, ME
8% off
Price is S$1,582
S$1,582
S$226 per night
includes taxes & fees
Image gallery for Art Haven Coastal Retreat
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Art Haven Coastal Retreat
Brooksville, ME
15% off
Price is S$1,838
S$1,838
S$263 per night
includes taxes & fees
Image gallery for Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine
1010 out of 10 rating
Exceptional
(10 reviews)
Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine
Sedgwick, ME
8% off
Price is S$1,124
S$1,124
S$161 per night
includes taxes & fees
Image gallery for Oceanfront apartment with private beach!
9.89.8 out of 10 rating
Exceptional
(90 reviews)
Oceanfront apartment with private beach!
Little Deer Isle, ME
7% off
Price is S$1,248
S$1,248
S$178 per night
includes taxes & fees
Image gallery for Waterfront Getaway Near Acadia w/ Spectacular View
1010 out of 10 rating
Exceptional
(13 reviews)
Waterfront Getaway Near Acadia w/ Spectacular View
Little Deer Isle, ME
7% off
Price is S$1,960
S$1,960
S$280 per night
includes taxes & fees
Image gallery for Beautifully Renovated 4 Bedroom Farmhouse
9.49.4 out of 10 rating
Exceptional
(91 reviews)
Beautifully Renovated 4 Bedroom Farmhouse
Brooksville, ME
8% off
Price is S$2,153
S$2,153
S$308 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Main Street
Spacious Cottage in Castine
Sleeps 6 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Welcome to The Wonky Donkey! Where life can relax with a little humor & sanity
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peaceful waterfront home on quiet cove with outdoor sauna near shops & hiking
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
8 reviews(8 reviews)
The Captain's Cottage is nestled near the shore of the tidal Bagaduce River.
Sleeps 5 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
15 reviews(15 reviews)
Classic Coastal Maine Retreat with Private Beach & Spectacular Waterfront Views
Sleeps 12 · 7 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Privately owned water view cottage with fabulous views of Penobscot Bay!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value