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Bennington Holiday Rentals

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46 rentals in Bennington.
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Perfect Getaway Home  In The Monadnock Region of NH, holiday rental in Bennington

Perfect Getaway Home In The Monadnock Region of NH

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr - Riverside Reflections. Peaceful Pines., holiday rental in Bennington

Tentrr - Riverside Reflections. Peaceful Pines.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Grand Victorian Home on 3 Landscaped Acres in a Rural Village Setting, holiday rental in Bennington

Grand Victorian Home on 3 Landscaped Acres in a Rural Village Setting

8 bedrooms
9 bathrooms
Sleeps 18
Match: Sleeps
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Spectacular Log Home with Private Lake Access, holiday rental in Bennington

Spectacular Log Home with Private Lake Access

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Log Home In Secluded Lake Ashuelot Estates, holiday rental in Bennington

New Log Home In Secluded Lake Ashuelot Estates

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Bennington

Sprawling, secluded gourmand's large cottage at base of Mt Monadnock

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cobb Hill Estate - 6 bedroom house sleeps 15 on 750 acre property!, holiday rental in Bennington

Cobb Hill Estate - 6 bedroom house sleeps 15 on 750 acre property!

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Little Red Wing - 1950's Lake cottage, holiday rental in Bennington

Little Red Wing - 1950's Lake cottage

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful lakefront log home nestled in the pines, holiday rental in Bennington

Beautiful lakefront log home nestled in the pines

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Hampshire lakefront  cottage in private association., holiday rental in Bennington

New Hampshire lakefront cottage in private association.

3 bedrooms
2 bathrooms
Sleeps 18
Match: Sleeps
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Secluded Vacation Home with direct lake frontage  on Contoocook Lake in NH, holiday rental in Bennington

Secluded Vacation Home with direct lake frontage on Contoocook Lake in NH

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakeside home. Fishing, paddle boarding, swimming, and easy lake  fun., holiday rental in Bennington

Lakeside home. Fishing, paddle boarding, swimming, and easy lake fun.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Camp on Granite Lake, holiday rental in Bennington

Camp on Granite Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Chicken Farmer I Still Love You., holiday rental in Bennington

Chicken Farmer I Still Love You.

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Bennington

Secluded Architect designed House - Monadnock Region - Great Escape

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Waterfront Cottage On Beautiful Lake Todd, holiday rental in Bennington

Cozy Waterfront Cottage On Beautiful Lake Todd

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming log cabin 'Lake Escape' on Highland Lake in Stoddard, NH....., holiday rental in Bennington

Charming log cabin 'Lake Escape' on Highland Lake in Stoddard, NH.....

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful  Log Cabin Overlooking Blaisdell  Lake! Sleeps 12, Private Beach, holiday rental in Bennington

Beautiful Log Cabin Overlooking Blaisdell Lake! Sleeps 12, Private Beach

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Lemon Drop Cottage a private cottage getaway, holiday rental in Bennington

Lemon Drop Cottage a private cottage getaway

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront all-season beauty and fun!, holiday rental in Bennington

Lakefront all-season beauty and fun!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful, Relaxing Setting. (Sanitized), holiday rental in Bennington

Beautiful, Relaxing Setting. (Sanitized)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage Country Get Away, holiday rental in Bennington

Cottage Country Get Away

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Mountain Views, Near Hiking, Art & Culture, Golf, Skiing, Restautant, holiday rental in Bennington

Spectacular Mountain Views, Near Hiking, Art & Culture, Golf, Skiing, Restautant

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded, Lakeside, Split-log Cottage with Fireplace, Rowboat, holiday rental in Bennington

Secluded, Lakeside, Split-log Cottage with Fireplace, Rowboat

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mil Bryn Lodge of Deering, holiday rental in Bennington

Mil Bryn Lodge of Deering

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cabin: Private Hot Tub, Walk to Pats Peak Ski Area, holiday rental in Bennington

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Weare Cottage w/ Fire Pit & Kayaks, holiday rental in Bennington

Waterfront Weare Cottage w/ Fire Pit & Kayaks

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Central A/C and Fast WiFi in the Sunapee Region, one level 1400sf with 3 BRs, holiday rental in Bennington

Central A/C and Fast WiFi in the Sunapee Region, one level 1400sf with 3 BRs

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Newly renovated -- Beautiful waterfront house in Henniker ,NH, holiday rental in Bennington

Newly renovated -- Beautiful waterfront house in Henniker ,NH

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Sunapee area - lakeside cottage trio on Sand Pond, holiday rental in Bennington

Sunapee area - lakeside cottage trio on Sand Pond

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!, holiday rental in Bennington

Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Lakeside Francestown Home w/ Private Dock & Porch!, holiday rental in Bennington

Lakeside Francestown Home w/ Private Dock & Porch!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Stunning & Scenic 2BR w/ Resort Pool Near Ski Area, holiday rental in Bennington

Stunning & Scenic 2BR w/ Resort Pool Near Ski Area

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning & Scenic 1BR w/ Resort Pool and Close to Ski Area, holiday rental in Bennington

Stunning & Scenic 1BR w/ Resort Pool and Close to Ski Area

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Deer Valley Retreat, Lovely Log Cabin, holiday rental in Bennington

Deer Valley Retreat, Lovely Log Cabin

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Bradford Home - 8 Miles to Mt. Sunapee!, holiday rental in Bennington

Historic Bradford Home - 8 Miles to Mt. Sunapee!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Robin's Nest' Cottage w/ Hot Tub - Near Lake, holiday rental in Bennington

Robin's Nest' Cottage w/ Hot Tub - Near Lake

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - The Lost Boys Hideout, holiday rental in Bennington

Tentrr Signature Site - The Lost Boys Hideout

1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Wally Meadows at Purgatory Falls, holiday rental in Bennington

Tentrr Signature Site - Wally Meadows at Purgatory Falls

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - The Lost Boys Hideout Rock'n Summer, holiday rental in Bennington

Tentrr Signature Site - The Lost Boys Hideout Rock'n Summer

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!, holiday rental in Bennington

Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!, holiday rental in Bennington

NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!

8 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
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Lakefront Weare House w/ Private Dock & Fire Pit!, holiday rental in Bennington

Lakefront Weare House w/ Private Dock & Fire Pit!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Townhouse in La Savina, holiday rental in Bennington

Townhouse in La Savina

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Luxe Riverfront Cottage w/ Dock by Lake Horace!, holiday rental in Bennington

Luxe Riverfront Cottage w/ Dock by Lake Horace!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Jaffrey Cottage w/ Mount Monadnock Views!, holiday rental in Bennington

Charming Jaffrey Cottage w/ Mount Monadnock Views!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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