Family-friendly holiday rentals in Woolwich

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Top-rated family-friendly rentals in Woolwich

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Flat in East End

4.96 out of 5 average rating, 543 reviews

Peaceful Oasis on Munjoy Hill -1st flr/3BR+parking

Enjoy this spacious, light-filled 3BR/1 bath 1st-floor apartment with tasteful art, contemporary furnishings, and a well-appointed kitchen. -Relax in the serene garden w/ outdoor seating. -Just a 5-minute walk to the Eastern Promenade with its food trucks, beach, & scenic trails. -Nearby are bakeries, cafes, world-class restaurants and popular breweries. -A 15-minute walk takes you to the Old Port. Discover the best of Portland, then return to A Peaceful Oasis, a place to truly call home.

Superhost

Flat in Damariscotta

4.85 out of 5 average rating, 102 reviews

Cottrill House on Damariscotta River #2

A convenient and newly renovated apartment. Enjoy the mid-coast in down town Damariscotta Maine. Private entrance, two bedrooms, private bathroom, living room, kitchen and dinning room. Private back yard with views over the Damariscotta River. Walk to unique restaurants and shops. Rent a kayak or a paddle board across the street and enjoy the beautiful views of the Damariscotta River. Only, 25 minutes away from Pemaquid Point and Beach. 32 miles to Popham Beach and Reid State Park. No smoking!

Guest favourite

Home in South Portland

4.91 out of 5 average rating, 116 reviews

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Guest favourite

Home in Buxton

4.88 out of 5 average rating, 126 reviews

Charming 4 bedroom lake front, with private beach

Will not consider less than weekly rentals for July and August and the last week in June.The house sits 80 ft off the lake. It has over 150 ft of lake shore and own private beach. We supply several kayaks paddle boards canoes and tubes . You will be required to sign a waiver to use them and you Must wear lifejackets .The home is located down a private gravel road .We are only 20 miles from the city of Portland, Old Orchard beach, Lake Sebago. Come explore and relax. 2 hours from Boston

Guest favourite

Flat in Falmouth

4.9 out of 5 average rating, 190 reviews

Falmouth 3br near Town landing

Enjoy the rocky coast of Maine with lobster rolls on Town Landing pier. Watch the Lobster fishers work and buy fresh lobster right off the boat. With Portland Maine’s iconic Foodie city with artisan brewers and fun dining and night life just down the road. (6.6 miles) Our classic New England Cape home is the perfect place to meet family and cook and eat around the counter in our amateur chef’s kitchen. Crack some fresh Lobster from Shaws on Rt One they are happy to cook them for you.

Superhost

Home in Portland

4.89 out of 5 average rating, 150 reviews

Great Modern Space and House

Beautiful house, updated and renovated by the owners. Very nice, quiet and friendly neighborhood on a dead end street. Clean, simple and modern home. Natural light in every space. Nice Bathrooms and updated Ikea kitchen. Open space in living room, very nice fence yard to watch from the living room and for kids to play. Wood and tile floors on the first floor. Carpet only on the bedrooms in the second floor. A lot of Storage and closets to make your stay very comfortable.

Guest favourite

Guest suite in Kennebunkport

4.99 out of 5 average rating, 206 reviews

Get back to nature in this new woodsy retreat.

Perfect for "leaf peeping". Beautiful 2nd floor two bedroom apartment with great light, nestled in the woods. Listen to the owls at night and wake to the birds chirping. Comfortably sleeps 5 in two queen beds and a twin XL bunk. Easy access to Goose Rocks Beach as well as Smith Preserve conservation trails for biking, hiking, trail running, snow shoeing and cross-country skiing. Located 6 miles from the center of Kennebunkport and 3 1/2 miles from Cape Porpoise.

Superhost

Flat in East End

4.82 out of 5 average rating, 135 reviews

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

Guest favourite

Flat in Waterville

5 out of 5 average rating, 104 reviews

Sweet Retreat: 3 BDR Stylish Home Mins To Colby

This spacious home of approximately 1,200 square feet is just 1.1 miles from I-95 and located on the ground floor of a charming, two family home completely renovated and tastefully furnished in 2020. Here the “modern design” and “charming rustic feel” mix perfectly. BONUS: Guests have access to the backyard! The private yard boasts a patio set, fire pit, garden, fence and trees along the property line.

Guest favourite

Cabin in Raymond

4.97 out of 5 average rating, 179 reviews

Idyllic Winter Lakeside Cabin

Situated on a beautiful lake with 350 feet of private shoreline the cabin is ideal for family gatherings or a small group of friends, it is not available for parties and events. A seven day minimum stay is required for summer months. Cozy up with board games, a book and enjoy the tranquility. We have firewood on the property for you to use. The docks are not in the water from October to April.

Guest favourite

Home in Bethel

4.96 out of 5 average rating, 112 reviews

Sunday River Bethel Village ! Walk to Restaurants

2 Bdrm, 1 Bth, Cozy Rental located in Bethel Village. 400 yds from The Bethel Inn. Walk to Bethel Village Restaurants & Shops. Home is in residential area with plowed sidewalks and well lit street. Ideal for a mature quiet couple or similar who are into skiing / enjoying the Bethel area and respectful of the property and neighbors. small dog ok, no cats.

Superhost

Home in Paris

4.93 out of 5 average rating, 141 reviews

Just a get away!!

My place is close to great views - for fall time - half hour to ski area's -oxford casino 7 miles away - hour drive to Mt Washington or Portland - Plenty of hiking area's- Oxford plains speed way 3 miles - , restaurants and dining . Read all { House Rules } it's under things to know, on the bottom left, before making reservation - Thank You