Vacation Rentals in Little Ossipee Pond, ME: Compare 10+ Sites & Save

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28 Best Vacation Rentals in Little Ossipee Pond (Starting from $158)

Tranquility Lake Home
Tranquility Lake Home
House
ME, USA
1.0k from Little Ossipee Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$262
Average price / night
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LAKE HOME! HOT TUB, GYM, FREEgolf cart, 2 kitchens
LAKE HOME! HOT TUB, GYM, FREEgolf cart, 2 kitchens
House
East Waterboro Maine, ME, 04030, United States
0.5k from Little Ossipee Pond center

AC, Dryer, Fireplace, Fitness Equipment, Kitchen, Laundry, Patio

6 Bedrooms20 Guests
9.4

Superb

3 reviews

$2216
Average price / night
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Scenic Little Ossipee Lake Retreat with Grill!
Scenic Little Ossipee Lake Retreat with Grill!
House
North Waterboro, ME, USA
1.0k from Little Ossipee Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$476
Average price / night
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Scenic Little Ossipee Lake Retreat w/ Grill!
Scenic Little Ossipee Lake Retreat w/ Grill!
House
East Waterboro, ME, 04030, United States
1.0k from Little Ossipee Pond center

AC, Balcony, Barbecue, Fireplace, Free Parking, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$332
Average price / night
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Waterfront Lake Arrowhead Cabin with Dock and Fire Pit
Waterfront Lake Arrowhead Cabin with Dock and Fire Pit
House
North Waterboro, ME, USA
7.2k from Little Ossipee Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms10 Guests
New to Booking
$611
Average price / night
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Ossipee Lake house, pet friendly
Ossipee Lake house, pet friendly
House
Waterboro, ME, 04030, United States
1.4k from Little Ossipee Pond center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms10 Guests
8.0

Good

12 reviews

$466
Average price / night
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Camp Crescendo Rustic Waterboro Cabin By Lake
Camp Crescendo Rustic Waterboro Cabin By Lake
House
Acton, ME, USA
7.5k from Little Ossipee Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$286
Average price / night
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Ossipee lake beach house, pet freindly
Ossipee lake beach house, pet freindly
House
Waterboro, ME, 04030, United States
1.4k from Little Ossipee Pond center

Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms10 Guests
9.2

Superb

13 reviews

$418
Average price / night
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Crescent Corner
Crescent Corner
House
ME, USA
7.7k from Little Ossipee Pond center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms7 Guests
New to Booking
$493
Average price / night
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Modern Rustic Cabin - Walk to Lake & Trails - With Fire Pit - Serene Escape
Modern Rustic Cabin - Walk to Lake & Trails - With Fire Pit - Serene Escape
House
Waterboro, ME, 04087, United States
6.3k from Little Ossipee Pond center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$437
Average price / night
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Maine Fall Foliage Lakefront Home in Limerick!
Maine Fall Foliage Lakefront Home in Limerick!
House
Limerick, ME, USA
7.9k from Little Ossipee Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$686
Average price / night
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Family & pet friendly lakeside home with game room, close to park & pools
Family & pet friendly lakeside home with game room, close to park & pools
House
Lake Arrowhead, ME, 04061, United States
6.9k from Little Ossipee Pond center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms9 Guests
9.8

Exceptional

17 reviews

$299
Average price / night
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Lake & Leisure
Lake & Leisure
House
Limerick, ME, USA
9.1k from Little Ossipee Pond center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay, Family

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$537
Average price / night
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Lakefront cottage | Indoor Pools | Kayaks
Lakefront cottage | Indoor Pools | Kayaks
House
Waterboro, ME, 04061, United States
7.0k from Little Ossipee Pond center

Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$614
Average price / night
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Vacation Getaway or Home Base During Fishing Tournaments
Vacation Getaway or Home Base During Fishing Tournaments
House
Waterboro, ME, 04061, United States
7.1k from Little Ossipee Pond center

Barbecue, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

4 Bedrooms6 Guests
9.0

Fabulous

34 reviews

$295
Average price / night
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Lakeside Log Cabin W/Sandy Beach and Docks! Sleeps 6-8
Lakeside Log Cabin W/Sandy Beach and Docks! Sleeps 6-8
Cabin
NORTH WATERBORO, ME, 04061, United States
7.1k from Little Ossipee Pond center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom8 Guests
9.8

Exceptional

64 reviews

$323
Average price / night
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Lake Arrowhead lakefront retreat: beach, dock, boat, fish, relax, adventures
Lake Arrowhead lakefront retreat: beach, dock, boat, fish, relax, adventures
House
North Waterboro, ME, 04061, United States
7.1k from Little Ossipee Pond center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

32 reviews

$513
Average price / night
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'Knotty Kabin' Rustic Waterboro Cabin By Lake
'Knotty Kabin' Rustic Waterboro Cabin By Lake
Cabin
Waterboro, ME, 04087, United States
7.5k from Little Ossipee Pond center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms5 Guests
10.0

Exceptional

5 reviews

$259
Average price / night
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Relax and Enjoy the Way Life Should Be, Lake Front, \nNorth Waterboro, Maine
Relax and Enjoy the Way Life Should Be, Lake Front, \nNorth Waterboro, Maine
House
Waterboro, ME, 04061, United States
7.6k from Little Ossipee Pond center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
9.6

Exceptional

32 reviews

$397
Average price / night
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Lakefront | Indoor Pools | Kayaks
Lakefront | Indoor Pools | Kayaks
House
Waterboro, ME, 04061, United States
7.7k from Little Ossipee Pond center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$511
Average price / night
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Dock! Dog-Friendly Lakefront Gem in Southern Maine
Dock! Dog-Friendly Lakefront Gem in Southern Maine
House
Waterboro, ME, 04061, United States
7.7k from Little Ossipee Pond center

Barbecue, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Pool, Tennis Court, Toys

3 Bedrooms7 Guests
9.0

Fabulous

8 reviews

$295
Average price / night
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WATERFRONT DOG FRIENDLY 3 BR 2 BATH YEAR ROUND HOME
WATERFRONT DOG FRIENDLY 3 BR 2 BATH YEAR ROUND HOME
Cottage
Waterboro, ME, 04061, United States
7.7k from Little Ossipee Pond center

Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$381
Average price / night
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Lakefront Cabin: Woodstove, Firepit & Ice Fishing!
Lakefront Cabin: Woodstove, Firepit & Ice Fishing!
Cottage
Limerick, ME, 04048, United States
7.9k from Little Ossipee Pond center

Barbecue, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Toys

3 Bedrooms8 Guests
9.6

Exceptional

27 reviews

$481
Average price / night
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New Lakefront Timber Frame Cabin On Beautiful Lake Arrowhead!
New Lakefront Timber Frame Cabin On Beautiful Lake Arrowhead!
Cabin
Limerick, ME, 04048, United States
8.0k from Little Ossipee Pond center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$410
Average price / night
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Pet-Friendly Lakeside Escape: Private Indoor Pool, Fenced Yard, and Pet Friendly!
Pet-Friendly Lakeside Escape: Private Indoor Pool, Fenced Yard, and Pet Friendly!
House
Lyman, ME, 04002, United States
8.3k from Little Ossipee Pond center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms9 Guests
10.0

Exceptional

4 reviews

$628
Average price / night
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 Cozy Waterfront cottage with Private dock- dog friendly!
Cozy Waterfront cottage with Private dock- dog friendly!
House
Lyman, ME, 04002, United States
8.9k from Little Ossipee Pond center

AC, Barbecue, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
9.2

Superb

34 reviews

$243
Average price / night
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1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Cabin
Shapleigh, ME, 04076, United States
9.4k from Little Ossipee Pond center

Free Parking, Outdoor Space

1 Bedroom3 Guests
9.0

Fabulous

4 reviews

$158
Average price / night
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Other accommodation types in Little Ossipee Pond:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Little Ossipee Pond.

Little Ossipee Pond Vacation Rentals on the Map

Frequently Asked Questions

You can explore 28 verified vacation rentals in Little Ossipee Pond. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Little Ossipee Pond vary depending on the season, property size, and location. Rates typically start from around $158 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Little Ossipee Pond include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Little Ossipee Pond welcome pets. Currently, 17 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Little Ossipee Pond often include amenities such as Fireplace/Heating, Balcony/Terrace, and Kitchen. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.