Vacation rentals in Winslow

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars6 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.91 out of 5 average rating, 77 reviews

Four brightly colored Adirondack chairs surround a stone fire pit, positioned on a grassy area facing a calm body of water. A scenic view of clouds reflecting on the water's surface enhances the tranquil atmosphere.

Home in Stockton Springs

Oceanfront Home Acadia-Camden -Belfast

TimRating, 5 stars6 months ago

We had a wonderfully relaxing week at the cottage right on the water! It was cozy and comfortable with all the amenities one needs. Our hosts were very responsive, provided a compilation of restaurants and "things to see and do" in the area - a very useful guide. We had fun exploring our surrounding areas and ate some incredible food! A fun-filled, yet relaxing time away - perfect!! We would highly recommend a stay with Cynthia and Dana! Thank you - - -

4.98 out of 5 average rating, 47 reviews

A serene lakeside view is captured at sunset, showcasing the soft glow of the sun reflecting on the water. A wooden dining table with chairs is positioned on the deck, accompanied by a large umbrella, enhancing the inviting outdoor space.

Home in Liberty

Peaceful Lakeside Getaway with Hot Tub!

KathrynRating, 5 stars2 months ago

We stayed for a short weekend trip and the house was absolutely amazing! Everything was clean and organized. The hosts even left flowers, chocolate, and a gift card for ice cream. The house book made it simple to know how everything in the house works. The view from the hot tub was spectacular. The only downside was the restaurant that was recommended in the book (Must Be Nice) was closed even though their website said open. Hoping to get to try it the next time we stay here. I would recommend this house to anyone looking for a peaceful getaway.

4.96 out of 5 average rating, 24 reviews

A charming cottage is framed by lush green trees, showcasing its light yellow exterior and welcoming front door. The grassy area surrounding the home offers a tranquil setting, and the clear sky above adds to the serene ambiance.

Guesthouse in Islesboro

Milk House

AmyRating, 5 stars1 month ago

What a cute little bungalow. A one room wonder. Milk House was easy to get to and had a couple walks to ocean views. Right on the main road but very quiet. We were prepared for the limited kitchen & were able to make 3 fabulous dinners. Get ready to unwind & unplug.

Apartment in Carrabassett Valley

An outdoor corridor is shown, lined with wooden railings and covered in fresh snow. Natural sunlight filters through the trees in the background, creating a serene winter landscape. The corridor leads towards a doorway marked with the number 7.

4.67 out of 5 average rating, 6 reviews

Centrally located 1 bedroom condo on mountain!

HayleyRating, 5 stars2 months ago

Amazing location! Easy walk to the lift to access the base area. Easy walk to shops and restaurants. Condo was comfortable and well stocked. The gas fireplace was great when we lost power from the super high winds. All questions were answered promptly and communication was clear. Definitely a great place on the mountain to stay.

0 of 0 items showing

What guests are saying

Stunning 2BR Riverfront | Dock

4.68 out of 5 average rating, 164 reviews2 months ago

The perfect winter’s escape! We were looking for a weekend to slow down and this location was ideal. It was centrally located to places like Bath, Wiscasset, Freeport and Portland but also offered the perfect amount of privacy. Waking up to a gorgeous snow fall and looking out over the river through the homes generous windows with no other homes around felt like a dream. Other reviews mention difficulty with the driveway access but it was thoroughly plowed, even during the strom, so we could travel without issue. They left a box of Valentines chocolates for us which was such a lovely treat. Breakfast at Annabelle’s in Richmond was a local treasure. Would definitely stay in this perfect and serene location again!

Cabin in Bowdoinham

What guests are saying

Luxury Condo on Water's Edge in Boothbay Harbor

5 out of 5 average rating, 32 reviews4 weeks ago

A few times while wandering around midcoast Maine in late March, we were asked if this is when we usually came to vacation here. Yes, we are educators from the Southwest, and this was our spring break, so this is when we came to visit, but honestly, it is so peaceful this time of year. Especially Boothbay Harbor, and what we imagined while walking around the very quiet town would be a very different place in July! Our experience at Abby’s space was absolutely wonderful and serene in the spring. The thoughtful touches (thank you for the bottle of Maine wine and jar of blueberry jelly!) made it even more special. Thank you, we hope to be back one day.

Apartment in Boothbay Harbor

What guests are saying

Sheepscot Overlook Cottage

5 out of 5 average rating, 3 reviews9 months ago

We stayed at Jena's home and had a lovely time. The home was plenty big for our family which included my parents, my husband and I with our 16 month old. The upstairs bedroom was claimed by my parents as they arrived before we did...what a treasure! We did not use the basement, but truly it is almost another apartment within the home but separate and private. We felt right at home and especially enjoyed the front porch every evening during our stay. We appreciate the location and found amazing food at The Water's Edge Restaurant and Bar which is walking distance from Jena's house. Fantastic location!

Home in Edgecomb

What guests are saying

Classic Maine cottage on best street in town w/ AC

4.96 out of 5 average rating, 53 reviews7 months ago

We LOVED staying at this house! The location is perfect- to town and to the local park. Walking the neighborhood was one of our favorite things. Our party was small, so we didn’t use the whole space (bedrooms) but we felt so comfortable/ at ease in the space.

Home in Camden

What guests are saying

Midcoast Maine Coastal Retreat

4.86 out of 5 average rating, 7 reviews6 months ago

Comfortable historic cottage with a magnificent view in a working fishing community, exactly what we love about the coast of Maine. Very peaceful setting with an abundance of wildlife all around - great birding right from the porch. Very comfortable bed and great linens. Lots of great walks/hikes nearby for outdoor lovers, and plenty of dining and shopping just 20 minutes away in Bath. Well stocked kitchen had everything we needed. A woodburning fireplace was definitely a plus and we loved cozy fires in the evenings. Five Islands Lobster is a short and and very pleasant walk for great fresh seafood. We loved bringing lobsters back and steaming them for dinner. Charlie was extremely helpful and responsive. We look forward to a return stay!

Home in Georgetown

What guests are saying

Incredible 3BR Oceanview | Deck | W/D

4.9 out of 5 average rating, 20 reviews9 months ago

This is a very pretty, well decorated and maintained older home. It has a lovely and tranquil backyard and deck.The location is less than a 10 minute walk on sidewalks to the center of Booth Bay Harbor and less than a 5 minute car ride. Because it is a historic home there are some minor issues. There is only one shower in the home. It is located downstairs near the laundry. The shower works well and is new. There is a bathtub upstairs but it is under a slanted ceiling. A child or someone shorter than 5’2” can stand in this tub. This upstairs bathroom is the access to the largest bedroom. This is a little awkward but the positive features outweighed this minor inconvenience for us. We did have trouble with the front door lock on two occasions but Vacasa was very responsive and i know they are working on this problem. If I returned to this area I would rent this home again.

Home in Boothbay Harbor

What guests are saying

Cozy, Comfortable, welcoming With private suite

4.8 out of 5 average rating, 15 reviews2 months ago

Marks place made our trip to visit family very comfortable and convenient to visit in the middle of winter. Very cozy and inviting and Mark was very attentive to ensuring our check-in and stay was great. If your looking for a great stay in Skowhegan with plenty of space and accommodation look no further.

Home in Skowhegan

What guests are saying

Island Getaway

5 out of 5 average rating, 30 reviews6 months ago

When we planned this vacation, we were looking for a location that provided serenity, a beautiful view, and walkable areas to totally relax from hectic year. Brad and Kathy's place far exceeded our expectations in every way. Their warmth, friendliness and helpfulness were felt throughout the week. Everything from attending yoga classes, golfing at North Haven and delicious fresh lobsters. It was a great experience and one that we certainly would re-visit in the future. Brad and Kathy are not just super hosts they are "super, super hosts!"

Home in Vinalhaven

1 of 12 pages

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Winslow vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winslow's top sights

Colby College17 locals recommend

Colby Museum of Art45 locals recommend

Railroad Square Cinema21 locals recommend

Silver Street Tavern20 locals recommend

Mainely Brews Restaurant and Brewhouse19 locals recommend

Selah Tea Cafe17 locals recommend

Other great vacation rentals in Winslow

5 out of 5 average rating, 103 reviews

An outdoor seating area is presented with a spacious sectional sofa made of dark wicker, positioned under a covered patio. The lawn extends towards the private sandy beach and dock by the lake, with a view of kayaks and trees in the background.

Cottage in Belgrade

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

SarahRating, 5 stars5 months ago

This property was awesome we were all very happy with the location, amenities, price and host. Hillary was polite and very helpful. This trip almost didn’t happen as our previous reservation was canceled 12 hours before check in from a different host. Luckily Hillary saved the week with her quick response time and answering questions about sleeping situations etc. would stay here again in a heart beat highly recommend!

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

4.75 out of 5 average rating, 20 reviews

A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

NinaRating, 5 stars3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !

5 out of 5 average rating, 3 reviews

The sun sets over Great Moose Lake, casting warm orange and golden hues across the water's surface. Reflections of the sunlight dance on the rippling waves, while silhouettes of trees mark the shore in the distance.

Home in Hartland

The Great Moose in Stunning Maine Swim, Fish & Ka

KevinRating, 5 stars7 months ago

My kids and I had an amazing time during our Labor Day weekend stay. The neighbors were so friendly and nice. The house was beautiful and had everything we needed. A market nearby for quick things. Beautiful area, access to water was great. We even got to enjoy the Harmony Free Fair and fireworks! Great weekend thank you!

5 out of 5 average rating, 101 reviews

Two black Adirondack chairs are positioned around a stone fire pit on a stone patio. In the background, a serene view of Winnegance Creek is visible, framed by trees and a cloudy sky.

Home in Bath

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars2 months ago

The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

5 out of 5 average rating, 7 reviews

A tranquil lakeside scene features a spacious dock with outdoor seating under a large umbrella. Kayaks are positioned along the edge, while a serene sunset casts warm hues over the water. An American flag gently waves beside the dock, completing this peaceful view.

Cabin in Belgrade

Great Pond Getaway|Lakefront|Dock|Sunset Views

ElizabethRating, 5 stars7 months ago

Wonderful weekend stay w our adult children. Kitchen had everything we needed to make dinner. Views of the lake were stunning. We all enjoyed a swim and paddle in the kayaks.

Cabin in Carrabassett Valley

The open-concept kitchen features dark cabinetry with modern appliances. Sunlight streams in through large windows, illuminating the space. A dining table occupies one side, while a cozy living area is visible through the glass doors leading to the deck.

4.75 out of 5 average rating, 4 reviews

Scoot Cabin - On Shuttle Route!

Teresa Rating, 5 stars9 months ago

Definitely would book again love the place and everything