Vacation rentals in Cliff Island

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Top-rated vacation rentals in Cliff Island

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Top guest favorite

A spacious wooden deck is presented, featuring two black Adirondack chairs positioned comfortably. A small potted tree adds a touch of greenery, while the surrounding snowy landscape reflects a serene outdoor atmosphere.

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 favorite

A modern outdoor sauna, designed with a circular wooden structure, is illuminated from within. Its glass door opens to reveal a warm interior with seating and soft lighting, surrounded by a snowy landscape and tall trees in the evening light.

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

Guest favorite

An outdoor hot tub is positioned on a patio surrounded by grass and trees. Bubbles rise from the water, creating a serene ambiance. A grill is located nearby, suggesting options for outdoor meals. Views of the surrounding landscape in the background enhance the setting.

Home in Falmouth

4.88 out of 5 average rating, 258 reviews

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Top guest favorite

A light-filled kitchen area showcases a vintage-style stove and a dining table with tall stools. Wood flooring extends throughout the space, complemented by large windows allowing natural light. A cozy atmosphere is created by the muted color palette and simple furnishings.

Apartment in Yarmouth

4.96 out of 5 average rating, 139 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

Top guest favorite

A wooden rocking chair is positioned near a window, featuring a soft yellow throw draped over the backrest. A round gray cushion rests on the seat, adding a touch of comfort and style to the inviting corner.

Guesthouse in Cumberland

4.96 out of 5 average rating, 115 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 favorite

Yurt in Chebeague Island

4.98 out of 5 average rating, 135 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.

Top guest favorite

A modern kitchen area is illuminated by natural light streaming through a skylight and a large window. A stainless steel sink is positioned under the window, complemented by wooden counters and open shelving. A single orange chair adds a pop of color, enhancing the minimalist design.

Apartment in Portland

4.98 out of 5 average rating, 151 reviews

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Guest favorite

A cozy cottage is surrounded by greenery, featuring a combination of stone and wood accents. Large windows allow natural light to enter, while a welcoming entryway is flanked by blooming shrubs. The landscaped yard offers a peaceful setting among the trees.

Cabin in Freeport

4.97 out of 5 average rating, 510 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Superhost

Apartment in Portland

4.78 out of 5 average rating, 575 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 favorite

A bathroom doorway opens into a compact space featuring a white toilet and a small sink. Light blue walls create a soothing contrast with the warm wood flooring. A mirror and a few shelves are mounted above the sink, providing functional storage.

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 favorite

An aerial view showcases the lush greenery surrounding the Stone Isle guest house, with expansive water views of Casco Bay. The property is set amidst vibrant trees, and various islands can be seen in the calm blue waters, highlighting the peaceful coastal landscape.

Home in Yarmouth

4.95 out of 5 average rating, 121 reviews

Stone Isle. 8 acres next 2 little john preserve.

Nestled on 8 acres overlooking Casco Bay, the Stone Isle guest house has 2 bedrooms, 1 bathroom and amazing water views. The guest house includes an open plan layout with a full kitchen, living room (with sleeper sofa) and a dining table for 4. Last but not least the guest house is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!

Guest favorite

A light green door is positioned prominently against a softly painted wall. A small, wall-mounted shelf displays decorative items. Nearby, a wooden dining table with two chairs is illuminated by natural light filtering through a window with light, sheer curtains.

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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Other great vacation rentals in Cliff Island

Guest favorite

A well-lit staircase is surrounded by light-colored walls and features a polished wooden banister. Framed artwork adorns the walls, while a console table and lamp are positioned near the bottom of the stairs. A patterned rug runs along the floor below.

Private room in Peaks Island

4.84 out of 5 average rating, 226 reviews

Peaks Island stays with 2 night minimum

LindsayRating, 5 stars2 weeks ago

Lovely home on Peaks Island! Rhonda is such a warm, friendly host and went above and beyond to make sure we had everything we needed during our stay.

Top guest favorite

A charming cottage is showcased against a backdrop of lush greenery. Large windows reflect natural light, while vibrant flowers and greenery frame the entrance, enhancing the natural setting. The simple design features a light-colored exterior and a cozy, welcoming presence.

Guesthouse in Freeport

5 out of 5 average rating, 66 reviews

Mast Landing Cottage

RichardRating, 5 stars2 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 .

A bright bathroom featuring a classic white clawfoot tub and a matching white toilet. Natural light enters through a window, illuminating the wooden walls and blue flooring. Simple fixtures and a clean layout contribute to the modern feel of the space.

Home in Chebeague Island

4.88 out of 5 average rating, 17 reviews

Red House

NicholaiRating, 5 stars6 days ago

We had a fantastic stay at Luke's place on Chebeague. Unbeatable location, steps to the boat yard. Cozy cottage with all the amenities you need for a great stay. Biggest surprise of the weekend was the screened porch - spent hours enjoying meals, cocktails, card games, and other memories out there without bugs/ with a lovely water view. Overall, a magical weekend on the island and hope to be back soon!

Top guest favorite

A spacious bedroom is highlighted by large windows that allow natural light to fill the room. A comfortable bed is centered against a wall, and a textured area rug adds warmth to the hardwood floor. Double doors open to a private balcony overlooking greenery.

Guesthouse in Yarmouth

4.99 out of 5 average rating, 141 reviews

Private Guesthouse in the Woods

RachelRating, 5 stars4 days ago

We had a great stay here! The place was perfect location and in a very nice area. Very quiet and close by to a lot of things. Also, very clean!

Top guest favorite

A framed botanical illustration is displayed on a neutral wall, featuring various plant shapes. Below, a wooden surface holds decorative pottery in blue and pink hues, alongside a glass bottle with a dark green tint, a candle, and a small dish. A chandelier casts soft light above.

Apartment in Falmouth

4.99 out of 5 average rating, 72 reviews

Sweet 2-story 1910 Bungalow near Portland, Beaches

JoshuaRating, 5 stars1 week ago

Beautiful little house built onto or converted from part of the host's house. Very cozy and comfy, lots of interesting things inside the space too. Susan and Kyle were both very kind and they had made a helpful directory for the area. Easy drive to Portland with everything you needed nearby in Falmouth as well while not being in a busy area. Really nothing is missing from this location and we would recommend it to anyone visiting.

Guest favorite

An historical cemetery marker stands prominently in the foreground, reading 'Old Settlers Cemetery - South Portland's Oldest Landmark 1658.' The backdrop features a serene view of the water with sailboats gliding by, framed by lush green grass and trees.

Private room in South Portland

4.89 out of 5 average rating, 374 reviews

Airy Room in Antique Victorian - SOPO

HenriqueRating, 5 stars2 weeks ago

I thought it was great! It was exactly what the pictures and descriptions said it would be. The only thing I would watch out for is if you get the AIRY room it does face the street so you can hear cars passing by. I didn’t wake up at night because of it but I’m also not a light sleeper so it might be different for you. But like I said. This was probably the most accurate depiction of any place I’ve ever stayed at. So if it looks good to you on the app it’ll look good to you in person.

Cottage in Long Island

4.93 out of 5 average rating, 30 reviews

Grace Cottage

AngelaRating, 5 stars11 months ago

We enjoyed the unplugged, relaxing feel at the cottage (Wi-Fi was great - unplugged by choice😁) Steven and team were friendly and responsive. Short walk to the waterfront, lots of time exploring rocks and tide pools. Ferry travel was easier then expected and everyone we met in the area was friendly!

Superhost

A vibrant plate is displayed, featuring a whole red lobster alongside a cluster of clams and a cob of corn. A plastic cup of refreshing drink is positioned nearby, with condiment packets and napkins arranged on the green wire table.

Cabin in Cape Elizabeth

4.86 out of 5 average rating, 7 reviews

Serene, ocean front cottage.

PhoebeRating, 5 stars3 weeks ago

Michael’s place is a sanctuary filled with local art and whimsical artifacts. Very pleasing space. Lots of outdoor seating areas possible and a stunning view across the path directly to the water. We had coffee on the rocks with the sun sparkling on the waves. Morning birdsong in the quiet of a peaceful setting away from all traffic. There are beautiful area beaches, and Portland is full of great food and fun including amazing farmers markets. We loved it!!!

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Vacation rentals in Cliff Island

Top-rated vacation rentals in Cliff Island

Vacation rentals for every style

Popular amenities for Cliff Island vacation rentals

Other great vacation rentals in Cliff Island

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