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Ossipee Holiday Rentals

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50 rentals in Ossipee.
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Cozy Lake Ossipee All Season Cabin, holiday rental in Ossipee

Cozy Lake Ossipee All Season Cabin

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tranquility & Serenity  The most restfull place on Ossipee Lake - What a beach, holiday rental in Ossipee

Tranquility & Serenity The most restfull place on Ossipee Lake - What a beach

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ossipee Lake waterfront on Broad Bay by the sandbar, holiday rental in Ossipee

Ossipee Lake waterfront on Broad Bay by the sandbar

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Rustic Comfort On A Mountain Lake, holiday rental in Ossipee

Rustic Comfort On A Mountain Lake

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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New listing! Lakefront retreat w/magnificent lake view - family dog is welcome!, holiday rental in Ossipee

New listing! Lakefront retreat w/magnificent lake view - family dog is welcome!

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home with Beautiful..kkmkmokmioi  Beach.mmi ***. on Ossipee Lakek.kmk, holiday rental in Ossipee

Waterfront Home with Beautiful..kkmkmokmioi Beach.mmi ***. on Ossipee Lakek.kmk

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Year Round Waterfront Get-Away On Ossipee Lake, holiday rental in Ossipee

Year Round Waterfront Get-Away On Ossipee Lake

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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LARGE Lake Home. SANDY BEACH Access. PERFECT for Families with KIDS!  Golf!, holiday rental in Ossipee

LARGE Lake Home. SANDY BEACH Access. PERFECT for Families with KIDS! Golf!

3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Mountain Views and Farm Animals, holiday rental in Ossipee

Tentrr Signature Site - Mountain Views and Farm Animals

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Scheduling Fall and Winter weekends away - PRISTINE 4 BEDROOM LAKESIDE CONDO, holiday rental in Ossipee

Scheduling Fall and Winter weekends away - PRISTINE 4 BEDROOM LAKESIDE CONDO

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful waterfront getaway full of attractions year round!, holiday rental in Ossipee

Peaceful waterfront getaway full of attractions year round!

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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900' lake frontage; Spacious 2 bedroom with loft, holiday rental in Ossipee

900' lake frontage; Spacious 2 bedroom with loft

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Waterfront Cottage With Dock On Berry Bay, holiday rental in Ossipee

Private Waterfront Cottage With Dock On Berry Bay

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Wentworth Rental - Wolfeboro, New Hampshire, holiday rental in Ossipee

Lake Wentworth Rental - Wolfeboro, New Hampshire

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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08-9 Lake Winnipesaukee (max 8) 5 min walk to Bay- FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

08-9 Lake Winnipesaukee (max 8) 5 min walk to Bay- FREE BIKES KAYAKS WOOD & WIFI

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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4 Season Cozy log Cabin/Lake/fire pit/game room/, holiday rental in Ossipee

4 Season Cozy log Cabin/Lake/fire pit/game room/

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ossipee Lake Waterfront Condo, holiday rental in Ossipee

Ossipee Lake Waterfront Condo

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Wolfeboro Lakehouse Retreat, holiday rental in Ossipee

Wolfeboro Lakehouse Retreat

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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LAKE-FRONT! Your own PRIVATE BEACH & DOCK on PRIVATE Peninsula, holiday rental in Ossipee

LAKE-FRONT! Your own PRIVATE BEACH & DOCK on PRIVATE Peninsula

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake Ossipee Townhouse, holiday rental in Ossipee

Lake Ossipee Townhouse

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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11 Mt. Washington Lake (max 6) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

11 Mt. Washington Lake (max 6) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious lakefront home w/screened-in porch, jet tub & firepit, holiday rental in Ossipee

Spacious lakefront home w/screened-in porch, jet tub & firepit

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Chalet in the white mountain region., holiday rental in Ossipee

Lovely Chalet in the white mountain region.

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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07 Squam Lake Cottage (max 3) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

07 Squam Lake Cottage (max 3) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Amazing 360 degree views of lakes and mountains, holiday rental in Ossipee

Amazing 360 degree views of lakes and mountains

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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16 Victorian-3 Floors (max 14) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

16 Victorian-3 Floors (max 14) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Charming dog-friendly cottage w/large yard, fireplace & lake access!, holiday rental in Ossipee

Charming dog-friendly cottage w/large yard, fireplace & lake access!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Amazing mountain views and Animals in the Lakes Region, holiday rental in Ossipee

Amazing mountain views and Animals in the Lakes Region

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wakefield Cottage: Private Dock on Pine River Pond, holiday rental in Ossipee

Wakefield Cottage: Private Dock on Pine River Pond

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lakefront Wakefield Cottage w/ Deck & Water Views!, holiday rental in Ossipee

Lakefront Wakefield Cottage w/ Deck & Water Views!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Retreat ~ 1 Mile to Ossipee Lake Marina!, holiday rental in Ossipee

Charming Retreat ~ 1 Mile to Ossipee Lake Marina!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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10 Lake Wentworth Cottage (max 4) 5 min walk to Bay-FREE BIKES KAYAKS WOOD& WIFI, holiday rental in Ossipee

10 Lake Wentworth Cottage (max 4) 5 min walk to Bay-FREE BIKES KAYAKS WOOD& WIFI

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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04 Brewster Pond Lodge (max 6) 5 min walk to Bay-FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

04 Brewster Pond Lodge (max 6) 5 min walk to Bay-FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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03 Loudon Pond Lodge (max 6) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

03 Loudon Pond Lodge (max 6) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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05-6 Portsmouth Pond Ldg (max 8) 5 min walk to Bay-FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

05-6 Portsmouth Pond Ldg (max 8) 5 min walk to Bay-FREE BIKES KAYAKS WOOD & WIFI

2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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12 Conway Lake Cottage (max 4) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

12 Conway Lake Cottage (max 4) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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01-2 Castle in the Clouds (max 8) 5 min walk to Bay-FREE BIKES KAYAKS WOOD, WIFI, holiday rental in Ossipee

01-2 Castle in the Clouds (max 8) 5 min walk to Bay-FREE BIKES KAYAKS WOOD, WIFI

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lake Winni - WF - 371, holiday rental in Ossipee

Lake Winni - WF - 371

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ossipee Lake Cottage w/ Screened Porch & Fire Pit!, holiday rental in Ossipee

Ossipee Lake Cottage w/ Screened Porch & Fire Pit!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Seventh Tee on Indian Mound Golf Course, holiday rental in Ossipee

Seventh Tee on Indian Mound Golf Course

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Lava Rock, holiday rental in Ossipee

Tentrr Signature Site - Lava Rock

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Center Ossipee Pet-Friendly Cottage w/ Dock!, holiday rental in Ossipee

Center Ossipee Pet-Friendly Cottage w/ Dock!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Dreamy Lakefront Getaway with Beach & Hot Tub, holiday rental in Ossipee

NEW! Dreamy Lakefront Getaway with Beach & Hot Tub

7 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps
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NEW! Bright Lake Winnipesaukee Home - Walk to Town, holiday rental in Ossipee

NEW! Bright Lake Winnipesaukee Home - Walk to Town

5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Win-win!  Relax at our place or relax at the lake, holiday rental in Ossipee

Win-win! Relax at our place or relax at the lake

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Black Snout, holiday rental in Ossipee

Tentrr Signature Site - Black Snout

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Cozy & Updated Apt Near Lake Winnipesaukee!, holiday rental in Ossipee

NEW! Cozy & Updated Apt Near Lake Winnipesaukee!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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13 Caretaker’s Studio (max 3) 5 min walk to Bay- FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

13 Caretaker’s Studio (max 3) 5 min walk to Bay- FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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15 Victorian-2 Floors (max 10) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

15 Victorian-2 Floors (max 10) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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14 Victorian-1st Floor (max 3) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI, holiday rental in Ossipee

14 Victorian-1st Floor (max 3) 5 min walk to Bay - FREE BIKES KAYAKS WOOD & WIFI

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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