Holiday rentals in Windham

4.99 out of 5 average rating, 396 reviews

Cottage in Pownal

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.

4.94 out of 5 average rating, 140 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Superhost

4.7 out of 5 average rating, 67 reviews

The "Happy Hen House" cottage in lakes region

Choose to stay here! The cottage is close to restaurants, shopping, arcades, miniature golf & swimming. Stay in this cozy classic cottage that includes 2 semi-private bedrooms (no doors), one with a queen size bed, the other with twin size bunk beds. On the main level, enjoy the sofa that opens to a full size bed; feel free to cook in the kitchen which is equipped w/stove, refrigerator, microwave, toaster & coffee maker. There is also a grill on the back deck w/plenty of outdoor seating.

4.98 out of 5 average rating, 120 reviews

Cabin in Standish

THE LILLIPAD.Off-grid A frame. Sebago lake region!

Take it easy in the woods at this cozy, off-grid A frame located in the Sebago Lakes Region. Kick back and relax around the fire while being "away from it all" yet still close by to great restaurants, beaches and more! This cabin is "off grid" and does not have running water or electricity. The space offers solar power that will power all lights, fans as well as charge devices. There is a battery operated pump that gives you potable water out of the sink. A porta potty is on property.

4.89 out of 5 average rating, 111 reviews

Flat in Cumberland Mills

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.

4.93 out of 5 average rating, 104 reviews

Guest suite in Standish

Steep Falls Escape, river & falls just steps away

Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

4.99 out of 5 average rating, 136 reviews

Flat in Windham

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

4.82 out of 5 average rating, 141 reviews

Cottage in Windham

Cozy camp near highland lake

If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

4.94 out of 5 average rating, 71 reviews

Flat in Westbrook

Cozy King bed apt near Portland with free parking

Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

4.92 out of 5 average rating, 185 reviews

Guest suite in Windham

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

4.93 out of 5 average rating, 30 reviews

Cabin in Windham

Cozy Private Lake Getaway (Seasonal)

If you love the traditional camp, this place is for you! Located on Forest Lake bordering Gray, Cumberland and Windham, Maine, this cozy place is off the beaten path yet only 20-30 minutes from Portland and all it has to offer. Perfect for a couple looking for a quiet lake getaway. The one bedroom has a full size bed. The living room couch pulls out to a queen size bed for extra guests.

Guest house in Cumberland

4.96 out of 5 average rating, 225 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

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Other great holiday rentals in Windham

5 out of 5 average rating, 8 reviews

Peaceful Garden Retreat

DeanRating, 5 stars8 months ago

This was exactly what we were looking for. After losing another airbnb booking somewhere else last minute we were very fortunate to find this one. Julie was so easy and responsive to deal with, friendly and welcoming. Her place was spacious and lovely, in a great location.

5 out of 5 average rating, 7 reviews

Flat in Gray

Bright and Cozy Studio

KatherineRating, 5 stars6 days ago

Clean beautiful little studio. Had everything you’d need including coffee! Comfortable bed and everything was very tidy and homey. Very responsive hosts as well.

4.97 out of 5 average rating, 33 reviews

Home in Gray

Little Sebago Lakefront Getaway

DanielRating, 5 stars8 months ago

Violeta and her space were amazing. The house was exactly as advertised and we felt right at home for our long weekend. We are looking forward to making this a yearly visit!

Superhost

5 out of 5 average rating, 5 reviews

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More

KimRating, 5 stars2 weeks ago

We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

4.83 out of 5 average rating, 6 reviews

Sebago Lake House

SavannahRating, 5 stars3 weeks ago

We stayed here for 5 nights and loved every second of it. Host was responsive when we had questions and was incredibly concise in his answers. It was cold and rainy while we stayed, but it didn’t make the lake any less beautiful! The sound of the rain on the water right outside the windows lulled my entire family and I to sleep. My dad loved the second floor balcony when it wasn’t raining, and the sitting area in the bedroom when it was. House is about 35-40 minutes outside of Portland, which was nice for us, as it meant getting to see the city while still being able to come back to the serene quiet of the house. Kitchen was also a very nice size and we were able to utilize the grill a couple of times as well. Overall, this house was perfect for a quiet getaway.

Farm stay in Gray

4.84 out of 5 average rating, 309 reviews

The Retreat at Crystal Lake Farm

AmieRating, 5 stars2 weeks ago

Jonathan was very communicative and a great host. Depending on needs I would stay here again. We were there for a graduation at Bates College. I would recommend this place for fall stays, hikes or visiting the near by lake. It's kind of far from Bates and Portland to make it super convenient to visit those places. Overall it was a very good value and Jonathan was a fantastic host, oh and the place was clean.

4.93 out of 5 average rating, 15 reviews

Sebago Lake Beach Paradise

ScottRating, 5 stars1 month ago

We had a great weekend with our family here following our son’s graduation from St. Joseph’s College. Great house!