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Jamesport Holiday Rentals

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50 rentals in Jamesport.
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Best kept secret in South Jamesport, holiday rental in Jamesport

Best kept secret in South Jamesport

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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On Jamesport Vineyard, Enjoy a Glass of Wine and Jazz in the Vines, holiday rental in Jamesport

On Jamesport Vineyard, Enjoy a Glass of Wine and Jazz in the Vines

3 bedrooms
3 bathrooms
Sleeps 6
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Stunning location  on 2 acre bayfront  in Jamesport, holiday rental in Jamesport

Stunning location on 2 acre bayfront in Jamesport

4 bedrooms
2 bathrooms
Sleeps 7
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Romantic Luxury Winery Apartment, holiday rental in Jamesport

Romantic Luxury Winery Apartment

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peconic Bay Private Beachfront Escape, holiday rental in Jamesport

Peconic Bay Private Beachfront Escape

5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful, Renovated Private Beach House, One Block from Bay, holiday rental in Jamesport

Beautiful, Renovated Private Beach House, One Block from Bay

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bay view beach house in North Fork Wine County, holiday rental in Jamesport

Bay view beach house in North Fork Wine County

2 bedrooms
2 bathrooms
Sleeps 6
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Cozy Cottage with private beach access, holiday rental in Jamesport

Cozy Cottage with private beach access

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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MATTITUCK, The North Fork's #1 Beach & Winery Town!, holiday rental in Jamesport

MATTITUCK, The North Fork's #1 Beach & Winery Town!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful North Fork Vacation Home - Wineries, Beaches, Waterpark, Dining., holiday rental in Jamesport

Beautiful North Fork Vacation Home - Wineries, Beaches, Waterpark, Dining.

3 bedrooms
2 bathrooms
Sleeps 9
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Escape the city! • Spectacular Beachfront Contemporary • Winter Rental: $7500/mo, holiday rental in Jamesport

Escape the city! • Spectacular Beachfront Contemporary • Winter Rental: $7500/mo

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront hidden gem with dock, holiday rental in Jamesport

Waterfront hidden gem with dock

3 bedrooms
4 bathrooms
Sleeps 6
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Eagles Nest - Private Hamptons Retreat by Beaches and Vineyards, holiday rental in Jamesport

Eagles Nest - Private Hamptons Retreat by Beaches and Vineyards

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Bay Beach 3bd Cottage. Walk To Beach And Jitney!, holiday rental in Jamesport

Bay Beach 3bd Cottage. Walk To Beach And Jitney!

3 bedrooms
1 bathroom
Sleeps 6
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It's All About This Sandy Private Association Bay Beach....A North Fork Gem!, holiday rental in Jamesport

It's All About This Sandy Private Association Bay Beach....A North Fork Gem!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New, luxury, open floor plan, pristine home centrally located with ALL amenities, holiday rental in Jamesport

New, luxury, open floor plan, pristine home centrally located with ALL amenities

4 bedrooms
6 bathrooms
Sleeps 9
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Waterfront Cottage 4, holiday rental in Jamesport

Waterfront Cottage 4

2 bedrooms
1 bathroom
Sleeps 4
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Waterfront Cottage 6, holiday rental in Jamesport

Waterfront Cottage 6

1 bedroom
1 bathroom
Sleeps 4
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North Fork 5 bed room home with forever farm view, holiday rental in Jamesport

North Fork 5 bed room home with forever farm view

5 bedrooms
2 bathrooms
Sleeps 10
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Steps to Beach and Spectacular Sunsets, holiday rental in Jamesport

Steps to Beach and Spectacular Sunsets

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Mattituck Beach Gen. Spacious & Gorgeously Renovated Beach House Steps to Bay., holiday rental in Jamesport

Mattituck Beach Gen. Spacious & Gorgeously Renovated Beach House Steps to Bay.

4 bedrooms
3 bathrooms
Sleeps 8
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Relaxing Home w/pool and private beach, holiday rental in Jamesport

Relaxing Home w/pool and private beach

2 bedrooms
2 bathrooms
Sleeps 5
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3 Bedroom Waterfront House on Peconic Bay Sleeps 6, holiday rental in Jamesport

3 Bedroom Waterfront House on Peconic Bay Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
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Wooded Serenity, Big Heated Pool, 5BR, Beautiful Beach, holiday rental in Jamesport

Wooded Serenity, Big Heated Pool, 5BR, Beautiful Beach

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Premier Waterfront Cottage 3, holiday rental in Jamesport

Premier Waterfront Cottage 3

2 bedrooms
1 bathroom
Sleeps 4
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Premier Waterfront Cottage 1, holiday rental in Jamesport

Premier Waterfront Cottage 1

2 bedrooms
1 bathroom
Sleeps 4
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Quaint Seaside Retreat With Full Gym, holiday rental in Jamesport

Quaint Seaside Retreat With Full Gym

4 bedrooms
3 bathrooms
Sleeps 10
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Cottage with a Modern European Edge, holiday rental in Jamesport

Cottage with a Modern European Edge

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Premier Waterfront Cottage 2, holiday rental in Jamesport

Premier Waterfront Cottage 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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5 bedroom/5 bath large secluded property on over an acre, holiday rental in Jamesport

5 bedroom/5 bath large secluded property on over an acre

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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WALK TO BEACH - HAMPTONS WITHOUT THE HASSLE, holiday rental in Jamesport

WALK TO BEACH - HAMPTONS WITHOUT THE HASSLE

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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150 ft to Private Beach, Nature Sanctuary Peconic Bay, holiday rental in Jamesport

150 ft to Private Beach, Nature Sanctuary Peconic Bay

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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North Fork cottage getaway with private beach, holiday rental in Jamesport

North Fork cottage getaway with private beach

4 bedrooms
2 bathrooms
Sleeps 9
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Charming Hampton Home, holiday rental in Jamesport

Charming Hampton Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Affordable East End home for beaches, golf, boating, wineries, antiquing, dining, holiday rental in Jamesport

Affordable East End home for beaches, golf, boating, wineries, antiquing, dining

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Hamptons Beach Round House with infinity pool & hot tub, holiday rental in Jamesport

Hamptons Beach Round House with infinity pool & hot tub

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Sea view beach house North Fork Vineyards Farm Stands Your own Private Beach!, holiday rental in Jamesport

Sea view beach house North Fork Vineyards Farm Stands Your own Private Beach!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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August in the Hamptons, holiday rental in Jamesport

August in the Hamptons

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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piece of Heaven, holiday rental in Jamesport

piece of Heaven

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Family Getaway Vacation Home In Wine Country, holiday rental in Jamesport

Family Getaway Vacation Home In Wine Country

5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Sand Dollar North Fork Beach House Vineyards, Farm Stands, Kayaks, holiday rental in Jamesport

Sand Dollar North Fork Beach House Vineyards, Farm Stands, Kayaks

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront in Mattituck, holiday rental in Jamesport

Waterfront in Mattituck

4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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The Perfect Setting for a Magical Summer, holiday rental in Jamesport

The Perfect Setting for a Magical Summer

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Jamesport Sound front beach house, holiday rental in Jamesport

North Jamesport Sound front beach house

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Modern Barn Loft in North Fork, ***. Wine Country in backyard Farm stands, holiday rental in Jamesport

Modern Barn Loft in North Fork, ***. Wine Country in backyard Farm stands

3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront Shared Guest House Suite 2, holiday rental in Jamesport

Waterfront Shared Guest House Suite 2

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage in the woods, steps from bay, holiday rental in Jamesport

Cottage in the woods, steps from bay

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Northfork meets midcentury country experience, holiday rental in Jamesport

Northfork meets midcentury country experience

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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North Fork Oasis by the Sea Heated Pool high end Hot tub steps to beach!, holiday rental in Jamesport

North Fork Oasis by the Sea Heated Pool high end Hot tub steps to beach!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Hamptons Waterfront Bungalow with private entrance, holiday rental in Jamesport

Amazing Hamptons Waterfront Bungalow with private entrance

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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