Vacation rentals in Little Ossipee Pond

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Top-rated vacation rentals in Little Ossipee Pond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Loft in Kennebunk

4.96 out of 5 average rating, 143 reviews

Private Modern Loft featured in Maine Home+Design

Experience the tranquility of staying in a PRIVATE STUDIO LOFT IN SEPARATE BLDG. overlooking 13 acres of private land abutting 600 acres of Alewive Brook Preserve while being 20 minutes to several area beaches and swimming lakes. The land is full of walking trails, fishing pond, biking trails and is conveniently only 7 minutes from the highway. Immaculate with wood floors, comfy queen size bed with Tempur-pedic mattress , 400 thread count soft 100 % cotton sateen sheets and high speed Internet.

Mar 16 – 23

$111 per night

Guest favorite

Guesthouse in Acton

4.96 out of 5 average rating, 224 reviews

The LOTUS welcomes you, your home away from home

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna (extra $111 per day) heated outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding will let you get some much needed rest. Enjoy walks on our 12 ac property or any of the lakes near by for any kind of year round outdoor experience. Welcome :)

Sep 12 – 19

$188 per night

Superhost

Treehouse in Sanford

4.9 out of 5 average rating, 436 reviews

The Canopy Treehouse, a Luxury Carbon Free Retreat

We have two new treehouses available - search "Sanford Maine" to find The Cliff House or The Sky Frame on Airbnb. Enjoy your tiny home in the trees! Although only 350 square feet, this home has everything you need for a delightful stay. Cook dinner in a full kitchen with a refrigerator, stove, oven, microwave, and coffeemaker. You have dinnerware, silverware, water and wine glasses, cookware, and all the essential kitchen accessories. Both the loft and sleeping pod provide queen beds.

Feb 8 – 15

$449 per night

Guest favorite

Home in Limerick

4.94 out of 5 average rating, 101 reviews

Lakefront Getaway

Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.

Dec 29 – Jan 5

$155 per night

Guest favorite

Farm stay in Buxton

4.96 out of 5 average rating, 202 reviews

Little River Flower Farm - Cottage

Post & Beam Cottage, rustic knotty pine interior. Five miles to Gorham Center close to USM, 20 minutes to St. Josephs College on Sebago Lake, easy 30 minute drive to Portland, 12 miles to the PWM Jetport. Centrally located to many of Maine's finest breweries: Sebago Brewing, Mast Landing, Funky Bow, Nonsuch, Sea Dog, Barrel Souls, Bissell Brothers. Many local hiking trails including trails right here at our farm. Portland boasts of the finest restaurants in the state.

Nov 14 – 21

$132 per night

Guest favorite

Home in Hollis

4.98 out of 5 average rating, 357 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Sep 24 – Oct 1

$160 per night

Guest favorite

Cottage in Buxton

5.0 out of 5 average rating, 119 reviews

Peaceful Cottage Retreat on Maine Flower Farm

Come stay among the flowers! The Cottage at Ferris Farm is a beautifully restored cottage where guests can relax, explore nature, and experience staying on a working flower farm. Enjoy a cup of coffee overlooking the flower fields and spend the afternoon kayaking the Saco River. Located in Buxton, the Cottage is centrally located between the wonderful restaurant and brewery scene of Portland and the popular coastline beaches of Old Orchard/Saco.

Aug 21 – 28

$203 per night

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 138 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Oct 25 – Nov 1

$306 per night

Guest favorite

Apartment in Saco

4.97 out of 5 average rating, 164 reviews

Cozy , pet friendly, quiet one bedroom studio

Take it easy at this unique and tranquil getaway. Cozy, sunny studio has everything you might need. Great place to rest and recharge in between beach trips, convenient shopping, exploring. It is a walking distance from Grocery store, Cozy breakfast restaurant, and more. Just minutes away from art galleries, coffee shops and bakeries. Wifi, Netflix, Kitchenette , parking! and even a friendly golden retriever Luna available for petting :)

Mar 24 – 31

$111 per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 218 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Jul 10 – 17

$110 per night

Guest favorite

Cottage in Wakefield

4.93 out of 5 average rating, 142 reviews

Lake View Cottage / Fenced in Yard

Discover NH’s charm in our family-friendly cottage: Highlights: • Family and Pet-Friendly • Bright, recently renovated • Stunning lake views in a fantastic neighborhood Convenient Location: • Prime spot across from the lake • Use the boat launch for easy lake access Outdoor Adventures: • Ideal for fishing • Bring your own kayak or boat Winter Note: • Fenced yard may be inaccessible in winter.

Nov 4 – 11

$143 per night

Guest favorite

Home in Lebanon

4.96 out of 5 average rating, 239 reviews

Beautiful, Peaceful, Maine Getaway House

Kick back and relax in this beautiful Maine getaway. Romantic, Quiet, country setting. Pet friendly. Big yard and trails for you and your pets to roam. Outdoor seating w/hammock. Minutes away from boat launching area to rent party boats, kayaks and paddle boats. Winter sports on Milton 3 ponds close by. Seasonal fruit picking right in town. Skydive New England. Fall leaf peeping. Extended stays welcome

Mar 3 – 10

$119 per night