Holiday houses in Casco Bay

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Top-rated holiday rentals in Casco Bay

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Top Guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 396 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

Top Guest favourite

Cabin in Georgetown

4.99 out of 5 average rating, 135 reviews

Sauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 acres with a pond minutes from one of the best beaches in Maine. Unwind in your private outdoor cedar glass sauna w/forest views & refresh in our seasonal outside shower! * Minutes to Reid State Park & 5 Island🦞 * Fire Pit * Family Own & Run * Gas Grill * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Rain Shower * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * Smart TV * Generator

Top Guest favourite

Guesthouse in Cumberland

4.96 out of 5 average rating, 116 reviews

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

Top Guest favourite

Yurt in Chebeague Island

4.98 out of 5 average rating, 136 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Guest favourite

Tiny home in Bowdoinham

4.91 out of 5 average rating, 116 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Top Guest favourite

Guest suite in Saco

4.96 out of 5 average rating, 157 reviews

LunaSea Suite

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

Guest favourite

Apartment in Westbrook

4.89 out of 5 average rating, 111 reviews

Minutes to Portland | Spacious | One Bedroom

Conveniently located in the charming Cumberland Mills neighborhood of Westbrook, this spacious one bedroom Victorian apartment offers easy access to Portland, the jetport, the highway, Rock Row, and other Westbrook attractions. Delicious eateries, local breweries, and Riverbank Park are within walking distance. This apartment comes fully furnished with a comfortable queen bed in the bedroom, a dedicated workspace, a Pack n' Play, and a pullout sofa bed available upon request.

Superhost

Apartment in Portland

4.78 out of 5 average rating, 577 reviews

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

Guest favourite

Guest suite in Portland

4.92 out of 5 average rating, 282 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Guest favourite

Guesthouse in Brunswick

4.94 out of 5 average rating, 154 reviews

Modern Brunswick Cottage near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.

Top Guest favourite

Apartment in Harpswell

4.92 out of 5 average rating, 199 reviews

Comfortable studio apartment in quiet location

Peaceful, rural second story studio apartment. Near Middle Bay in beautiful Harpswell, Maine. Enjoy our farmer's porch or walks to the shore deck to look out over the water and enjoy a sunset or go the the shore for a swim in summer. Short distance to Brunswick and Bowdoin College, local restaurants. The host also teaches porcelain doll making. You could learn to make porcelain dolls while enjoying the Maine coast.

Guest favourite

Guest suite in South Portland

4.92 out of 5 average rating, 255 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

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Popular amenities for Casco Bay holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Casco Bay

Top Guest favourite

Guesthouse in Freeport

5 out of 5 average rating, 66 reviews

Mast Landing Cottage

RichardRating, 5 stars6 days ago

great location for freeport in being close to everything yet out of the business of the town on a well kept lot . guest house itself shaded by trees has the calm feeling sometimes missing in a lot of southern maine especially in the summer season . also good for guests with dogs as there is a wonderful dog walking path just up the street .

Superhost

Apartment in Portland

4.83 out of 5 average rating, 12 reviews

Roof Deck | Parking | 5 Min Downtown

AmberRating, 5 stars3 days ago

Great space and beautiful set up! The place is exactly as it looks in the photos. It’s located in a quiet and peaceful neighborhood, and is only a short drive to downtown Portland. A perfect rooftop deck to read on and catch some rays. The hosts were responsive and the instructions were clear. Very easy check in and check out process. Would highly recommend!

Top Guest favourite

Barn in Scarborough

5 out of 5 average rating, 17 reviews

Stunning 1 bedroom barn.

MariaRating, 5 stars7 months ago

I had a lovely stay at thr barn. Check in was smooth, space was very clean, the location was perfect. Lots of nature and beautiful park/trail at walking distance with a very quick drive to beach! Christopher and Nathalie are great hosts! They were responsive and also very accommodating with my needs. This is a wonderful Airbnb for a peaceful and serene nature retreat while also being close to Portland!

Top Guest favourite

Guesthouse in Yarmouth

4.99 out of 5 average rating, 142 reviews

Private Guesthouse in the Woods

ChristinaRating, 5 stars2 days ago

Exceeded expectations! The location is ideally located near Cousins Island and Yarmouth. Super clean, and relaxing. I loved the balcony that overlooks a gorgeous wooded view. The kitchen is well appointed. We were in town for a family grad party, and my son enjoyed the proximity to the bike path for a scenic run to the island. We were fortunate enough to meet Luna and Denis, who was very helpful with local recommendations. The location is very private and easy to get to. The check in process is clear and easy. The beds are clean and very comfortable. We look forward to returning.

Home in Phippsburg

5 out of 5 average rating, 4 reviews

Mid Coast Getaway w/ water views

KristenRating, 5 stars2 weeks ago

Fantastic stay this past weekend. Easy to find and flexible with check in. I got there an hour earlier than expected and it was no problem for me to go in early. Felt safe being a solo traveller. The views were insane! So so peaceful. Some considerations: Some outdoor comfortable seating would've been great. I could not lock anything because the locks of the sliders wouldn't open/close with the keys-I was afraid I would break a key off. So left wide open during the day. The couch, comfy, but stained. Only 2 towels were left-more would've been appreciated. I was freezing! So glad I brought an extra blanket. Leaky sink in kitchen. ZERO I mean ZERO water pressure-awful! Service is spotty in the area but the wifi was a big help. The price, views, communication, and flexibility cancels out any flaws of this place. With some TLC this place would be flawless. Thank you!

Home in Harpswell

4.82 out of 5 average rating, 141 reviews

Beautiful Designer's Hideaway on the Maine coast!

IveyRating, 5 stars3 weeks ago

Gorgeous house overlooking the sound! Very peaceful, clean, and a home with a lot of heart & gorgeous decor. Would love to stay here again for longer than a weekend! Can’t recommend enough!

Superhost