
House holiday rentals in Woolwich
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Top-rated house rentals in Woolwich
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Popular amenities for house rentals in Woolwich
House rentals with a pool

Treehouse Farm - Sebago
Great backyard with a pool, hot tub, fire pit and privacy with the woods.

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

Lovely home with hot tub and pool
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Riverfront Luxury in the woods, Million $ Views.
Property had amazing views. Inside was beautiful and very clean. Pond and river was nice. Host was quick with any question we had. would recommend.10/10

OOB Oasis - 5BR private Retreat w/ Pool
Great house! Very spacious, plenty of bathrooms, and fantastic location. Very easy to communicate with the owners and check in/out was simple. My minor only critique is that we wish the grill were a bit bigger and nicer. We wanted to grill one day, but we were a little disappointed and unable to do so due to the grill quality. Would definitely stay again!

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches
Top notch spot and host!! We had such a great time at Alexa’s lovely home! It was so cozy, beautifully decorated, modernized, and had all the essential items you’d need - plus it is completely pet friendly! Our dog loved the fenced in yard with a doggy door to get out to it. The sauna, endless pool, and hot tub are just amazing amenities to have on site - that sunroom was my favorite place in the house to say the least! Can’t say enough about it and Alexa, too! She is super friendly, responsive, and had great recommendations for fun and good food in the area. Overall, it was just a wonderful and relaxing experience for our first time on the Maine coast and we can’t wait to visit again!
Weekly house rentals

The Happy Harbor House-Walk to town!
Liz is a phenomenal host The home is newly remodeled and beautiful! It’s litterally steps away from the waterfront. She gave us lots of suggestions which we did including a stop in Camden on our way from BarHarbor for lunch at Camden deli and views from mt battie. We visited Maine Coastal Gardens and enjoyed the trolls and lush gardens (wish we could have stayed longer) and did a 4 1/2 hour whsle/ puffin tour no whale sittings but we saw lots of puffins, a seal and porpoise. Ended the day with dinner at ports of Italy Amazing food We would definitely stay here again only regret is we didn’t stay long enough

The Pink House on Echo Farm
Beautiful place and so close to booth bay harbor and botanical gardens Bring your boots because the property is amazing to walk and it is a bit muddy to the river but so worth it The views are incredible House came with super clear instructions for anything you could possibly need

Family Escape w/ Kayaks, Fire Pit, & Water Access
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out

Kens Cottage in Round Pond ME
Quaint Maine Coast cottage for two? Check! Mid-October retreat to peaceful location? Check! About as close to waterfront you can get without falling in? Check! Morning sunrise across the harbor with rose, pink, purple, blue neon colors? Check! Funky, Artsy, Unique cottage features (by all means, appreciate the Art Glass newel posts)? Check! Clean, cozy, comfortable and induces lazy R&R? Double Check!! Nearby places to explore, learn history, eat & drink hearty, hike, shop for treasures? Also double check!! My husband and I frequent the Pemaquid Peninsula during all seasons. Sometimes we camp, sometimes we find hidden gems to stay for a weekend...Ken's Cottage is a keeper...Triple Check!!! Thank You Kirsten for the wonderful hospitality!!! We will be in touch!!!

Maine Stowaway Carriage House
Perfect in every way! I have stayed at multiple air BnB’s and nothing compares to this house! Pictures do not do this place justice!! The location is awesome, secluded with a great view. One thing that stood out to me other than the awesome view and being secluded is that the house is stocked with everyday household essentials, other air BnBs I have stayed at never had the house stocked they way that this one does! I highly recommend this house to anyone that wants to visit south port!

Unique Octagonal House with Private Beach!
Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!

Luxury Waterfront Home with Dock - The Sea Eagle
The house was beautiful and in a great location. The owners were extremely responsive and kind! We had a wonderful weekend at this incredible house.

Beautiful Maine Lakeside Cottage
Very clean and Host was very responsive, the setting matched the description 100%. Peceful sleeping with the water hitting the beach and the call of the Loon heard throughout the night. Can’t wait to return another day!!
Private house rentals

2 Acre Waterfront w/Canoes & Kayaks, Game Room
If you want a private, well furnished home in the woods with fishing access on the stream and 2 fire pits this is your place!! Staying at this house made a work trip for my crew and I, feel like we were on vacation for 2 nights while staying there. Worth the money and great hosts!

New Modern Cottage with Ocean Views & Wildlife
We can’t say enough good things about this stay. We came for our honeymoon, and were met with flowers and a few other treats from the host as a gift. How sweet! As far as the property, the cottage is perfectly sized for two or three, and is designed delightfully. It is on a shared lot with the family’s primary residence , but feels very comfortable and private. A close by walk to the water as well. Inside, you will find everything you could ever need from pots and pans, spices, towels, and the best recommendations for the area. We’d build our own version of this cottage to take home with us if we could. We hope to one day be back and will always remember our amazing time in Harpswell.

Boothbay coastal home
Close to fun brewery across street , close to downtown area . Just stayed two nights was nice get away.

Sunset Waterfront Retreat • Cozy 3BR + Kids’ Nook
A five star setting in a true Maine oasis. If you're looking for a great , clean and comfortable house with a pondfront setting in a small Maine town, look no further. Every amenity you would hope for is there. Furniture is nice and lots of homey personal touches. Great bed which isn't always the case in even better AirBnBs. Hosts were good communicators and responses to questions came quickly. No complaint on anything. Dog friendly is a bonus!

Cozy Year Round Bungalow - Walk to Town!
We had a great time in Boothbay Harbor. We Loved the house and it's location. highly recommend staying. The weather was exactly what we wanted coming from Florida.

Boothbay area architectural gem
Very bright and modern home with comfy beds and plenty of space. It was close to our wedding venue and we had a wonderful time. Hosts were responsive when needed.

Coastal maine
Very clean with new furnishings and a well-equipped kitchen. Tucked away in a quiet, private spot that feels secluded but is actually close to everything - Boothbay Harbor, a terrific bakery, coffee shops, the local supermarket, craft beer, fine wine - the list goes on. A great place to stay!

Pinkham Cove - Water Front Cottage
Gorgeous location, comfortable house and amenities and friendly and responsive hosts. Couldn’t have asked for a more wonderful quiet vacation spot close to Boothbay Harbor!
Quick stats about house rentals in Woolwich
Total rentals
40 properties
Nightly prices starting at
₹3,425 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Sebago Lake
- Scarborough Beach
- Popham Beach State Park
- Surfside Beach
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- East End Beach
- Belgrade Lakes Golf Club
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- Funtown Splashtown USA
- Dunegrass Golf Club
- Freddy Beach
- Portland Museum of Art
- Crescent Beach State Park
- Maine Maritime Museum
- Portland Country Club
- Wolfe's Neck Woods State Park
- Bradbury Mountain State Park