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.

Jan 5 – 12

G$26,605 GYD per night

Guest favorite

Home in Acton

4.98 out of 5 average rating, 126 reviews

The ZEN welcomes you, your home away from home.

The goal is for you to relax, recharge, enjoy & breathe. We offer a private 3 person HOT TUB , seasonal outdoor warm shower& chiminea firepit , infrared SAUNA, 72" freestanding bathtub for the ULTIMATE spa experience. King bed with an adjustable & vibrating bed base. The cozy 600 sqf home is equipped with everything your heart could desire. Artistic Design around every corner. BOHO swings on the private porch. We abutt a 13 ac conservatory land with walking & hiking trails off the backyard.

Aug 22 – 29

G$46,882 GYD per night

Guest favorite

Guest suite in Conway

4.99 out of 5 average rating, 419 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

Sep 18 – 23

G$25,695 GYD 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.

Nov 21 – 28

G$107,329 GYD 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.

Mar 16 – 23

G$36,725 GYD per night

Guest favorite

Farm stay in Buxton

4.96 out of 5 average rating, 203 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.

Aug 17 – 24

G$30,589 GYD per night

Guest favorite

Home in Hollis

4.98 out of 5 average rating, 359 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 25 – Oct 2

G$38,067 GYD 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.

Jun 12 – 19

G$48,473 GYD per night

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 139 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

G$73,239 GYD per night

Guest favorite

Apartment in Saco

4.97 out of 5 average rating, 165 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 :)

Nov 7 – 14

G$26,514 GYD 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.

May 29 – Jun 5

G$26,381 GYD per night

Guest favorite

Home in Lebanon

4.96 out of 5 average rating, 240 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

Apr 3 – 10

G$28,006 GYD per night