Family-friendly vacation rentals in Sidney

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Sidney

  • Total vacation rentals

    Explore 50 vacation rentals in Sidney

  • Nightly prices starting at

    Sidney vacation rentals start at G$25,096 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,700 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Sidney vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Sidney rentals

  • 4.9 Average rating

    Sidney stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Sidney

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

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Top guest favorite
Cabin in Chesterville
5 out of 5 average rating, 200 reviews

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Top guest favorite
Cabin in Whitefield
5 out of 5 average rating, 129 reviews

Maybelle the Tiny Cabin on 100 acres

Maybelle is an 8x18 cabin with a full-size loft bed, a Cubic Mini Woodstove (wood provided), Natures Head Composting Toilet and Jetsetter massaging hot tub. Kayaks, paddle board, & canoe included . Hiking trails (some solar lit) surround your cabin. Outside is a fire pit and a quick path to the water. Maybelle's kitchen has all the cooking essentials and there's a small propane grill outside & the fire pit for cooking. Cell reception is okay in the cabin, wifi is from a Starlink booster!

Top guest favorite
A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.
Cabin in Georgetown
4.99 out of 5 average rating, 221 reviews

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Top guest favorite
A charming A-frame cabin is set amidst the lush greenery of the woods. The natural wooden exterior complements the surroundings, while two teal chairs invite guests to relax. A gravel pathway leads to the entrance, framed by large stones and trees casting gentle shadows.
Cabin in Oakland
4.98 out of 5 average rating, 142 reviews

Sister a-frame in Woods (A)

Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!

Guest favorite
A serene outdoor area is framed by lush greenery and trees, showcasing vibrant orange flowers in the foreground. A meandering stone path leads towards a gathering area in the distance, partially visible through the foliage.
Home in Sidney
4.87 out of 5 average rating, 112 reviews

Brook Ridge Retreat

Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 451 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Guest favorite
A serene lakeside view reveals calm waters reflecting the sky. Pine trees frame the scene, with a wooden railing suggesting a deck area. The landscape is peaceful, featuring a distant tree-lined shore under a clear blue sky.
Chalet in Belgrade
4.82 out of 5 average rating, 126 reviews

Visit Beautiful Home on Snow Pond

Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.

Top guest favorite
The cabin is viewed from the water, framed by lush greenery and tall trees. A spacious porch extends across the front, highlighting the cabin's inviting structure, while the calm water reflects the surrounding nature and the bright exterior of the building.
Cabin in Augusta
5 out of 5 average rating, 117 reviews

Price's Point - Cabin on the water

Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

Top guest favorite
A relaxing hot tub is positioned on a wooden deck surrounded by trees, overlooking the serene landscape. A person sits at the edge, holding a glass, with soft sunlight filtering through the foliage, creating a peaceful atmosphere.
Treehouse in Belgrade
5 out of 5 average rating, 135 reviews

SkyView Treehouse | Lakefront • Private Hot Tub

Welcome to your dream treehouse escape — tucked among the pines with stunning lake views, a private hot tub, and direct access to Belgrade Stream. Designed for couples, honeymooners, and small families, SkyView Treehouse offers a luxurious retreat in nature. Enjoy starry nights in the hot tub, cozy evenings by the fireplace, and peaceful mornings on your private deck. Rustic charm meets upscale comfort in this unforgettable lakeside getaway.

Top guest favorite
A spacious two-story home is showcased amidst a snowy landscape. Snow covers the roof and ground, while evergreen trees flank the entrance. Festive decorations accent the front door, and a gentle snowfall creates a serene atmosphere on the property.
Guest suite in Oakland
4.98 out of 5 average rating, 270 reviews

Cozy Studio Flat, Belgrade Lakes Region

Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.

Guest favorite
An outdoor deck features a dining table surrounded by four chairs and a large umbrella. Soft lighting illuminates the space, complemented by a cozy seating area near the edge of the deck. A well-maintained lawn extends beyond the deck.
Cottage in Belgrade
4.93 out of 5 average rating, 166 reviews

Lake Great Pond| Dog Friendly | Boat Launch

Welcome to Driftwood Cottage, nestled in a quiet lakeside community on Lake Great Pond. Perfect for families and pets, this home comfortably sleeps 8 and offers water access, a private boat slip, kayaks, and two fire pits. Enjoy lake views from the expansive deck in a peaceful lakeside community. Your ultimate Maine getaway awaits!

Guest favorite
A tranquil lakeside view showcases the calm waters of Great Pond, framed by lush trees. A private dock extends into the lake, and a grassy yard features seating options, including a picnic table. A yellow inflatable float is visible on the water in the distance.
Cottage in Belgrade
4.97 out of 5 average rating, 127 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

The Pinkhams Cove Lakeside Cottage on Great Pond (Golden Pond, Belgrade Lakes) is bright and welcoming inside. A beautiful interior and an inviting outdoor space with a private sandy beach makes this the perfect place for family and friends to make Maine memories. This location is wonderful to enjoy all of Maine’s seasons.

Popular amenities for Sidney family-friendly rentals

When is the best time to visit Sidney?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$76,124 GYDG$79,261 GYDG$75,078 GYDG$79,261 GYDG$60,648 GYDG$61,903 GYDG$66,086 GYDG$72,569 GYDG$64,204 GYDG$75,706 GYDG$79,261 GYDG$78,006 GYD
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