Oceanfront Rentals in Jonathan Young Windmill, MA: Compare 10+ Sites & Save

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  6.  Jonathan Young Windmill

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657 Best Oceanfront Rentals in Jonathan Young Windmill (Starting from $257)

Orleans Holiday House
Orleans Holiday House
House
Orleans, MA, USA
1.9k from Jonathan Young Windmill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Family

5 Bedrooms8 Guests
New to Booking
$262
Average price / night
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Peaceful waterview retreat with sunroom, AC, grill & amazing outdoor space
Peaceful waterview retreat with sunroom, AC, grill & amazing outdoor space
House
Eastham, MA, 02642, United States
0.2k from Jonathan Young Windmill center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$506
Average price / night
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Island Bay Bungalow
Island Bay Bungalow
House
Eastham, MA, USA
2.1k from Jonathan Young Windmill center

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

3 Bedrooms6 Guests
8.5

Very Good

2 reviews

$257
Average price / night
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Historic charmer on the water with a firepit, kayaks, bikes, & firepit
Historic charmer on the water with a firepit, kayaks, bikes, & firepit
House
Eastham, MA, 02642, United States
0.2k from Jonathan Young Windmill center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, No Smoking

3 Bedrooms6 Guests
9.4

Superb

13 reviews

$969
Average price / night
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Salty Ridge Station
Salty Ridge Station
House
Orleans, MA, USA
2.1k from Jonathan Young Windmill center

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

4 Bedrooms8 Guests
New to Booking
$632
Average price / night
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Waterfront Fun at this Huge Family Estate!
Waterfront Fun at this Huge Family Estate!
House
Eastham, MA, 02642, United States
0.3k from Jonathan Young Windmill center

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

11 Bedrooms23 Guests
10.0

Exceptional

12 reviews

$2437
Average price / night
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Namskaket Retreat
Namskaket Retreat
House
Orleans, MA, USA
2.4k from Jonathan Young Windmill center

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

3 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$619
Average price / night
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Newly updated spacious steps to water!
Newly updated spacious steps to water!
House
Eastham, MA, 02642, United States
0.3k from Jonathan Young Windmill center

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

2 Bedrooms4 Guests
9.4

Superb

20 reviews

$427
Average price / night
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Walk to Skaket Beach Charming Cottage with Deck
Walk to Skaket Beach Charming Cottage with Deck
House
Orleans, MA, USA
2.5k from Jonathan Young Windmill center

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

3 Bedrooms6 Guests
New to Booking
$629
Average price / night
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Waterfront amazing views near beaches!
Waterfront amazing views near beaches!
House
Eastham, MA, 02642, United States
0.3k from Jonathan Young Windmill center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
8.6

Fabulous

13 reviews

$599
Average price / night
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2 Bed 1 Bath Vacation home in Eastham
2 Bed 1 Bath Vacation home in Eastham
House
Eastham, MA, USA
3.6k from Jonathan Young Windmill center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms4 Guests
9.7

Exceptional

3 reviews

$321
Average price / night
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Cute Cottage Living by the Sea!
Cute Cottage Living by the Sea!
House
Eastham, MA, 02642, United States
0.3k from Jonathan Young Windmill center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.0

Fabulous

22 reviews

$335
Average price / night
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Areys Pond Point
Areys Pond Point
House
Orleans, MA, USA
3.7k from Jonathan Young Windmill center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

4 Bedrooms8 Guests
8.0

Good

1 reviews

$394
Average price / night
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Quintessential Captain's House w/ Water Views!
Quintessential Captain's House w/ Water Views!
House
Eastham, MA, 02642, United States
0.3k from Jonathan Young Windmill center

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

5 Bedrooms11 Guests
9.6

Exceptional

14 reviews

$762
Average price / night
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Cape Landing Cottage
Cape Landing Cottage
House
Brewster, MA, USA
4.8k from Jonathan Young Windmill center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$660
Average price / night
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Town Cove Coastal Chic
Town Cove Coastal Chic
House
Orleans, MA, 02653, United States
0.6k from Jonathan Young Windmill center

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

3 Bedrooms6 Guests
New to Booking
$845
Average price / night
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6 Mi to Beach Home with Deck in Brewster!
6 Mi to Beach Home with Deck in Brewster!
House
Brewster, MA, USA
6.0k from Jonathan Young Windmill center

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

3 Bedrooms8 Guests
New to Booking
$294
Average price / night
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Sweeping Water Views, Walk to Town, Outdoor Shower!
Sweeping Water Views, Walk to Town, Outdoor Shower!
House
Orleans, MA, 02657, United States
0.6k from Jonathan Young Windmill center

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

3 Bedrooms6 Guests
New to Booking
$557
Average price / night
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The Mansion at Ocean Edge Resort & Golf Club
The Mansion at Ocean Edge Resort & Golf Club
Resort
Brewster, MA, USA
6.2k from Jonathan Young Windmill center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, 5-star, Lodgings, Beach

70 Bedrooms22 Guests
8.5

Very Good

80 reviews

$790
Average price / night
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Waterfront on the Cove, NEW Kitchen and Central AC
Waterfront on the Cove, NEW Kitchen and Central AC
House
Orleans, MA, 02653, United States
0.6k from Jonathan Young Windmill center

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

3 Bedrooms7 Guests
9.8

Exceptional

14 reviews

$662
Average price / night
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Cape Cod Sunscape. Orleans
Cape Cod Sunscape. Orleans
House
Orleans, MA, 02653, United States
0.7k from Jonathan Young Windmill center

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

2 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$690
Average price / night
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Tranquil Eastham Waterfront Cottage Escape
Tranquil Eastham Waterfront Cottage Escape
Cottage
Eastham, MA, 02642, United States
0.8k from Jonathan Young Windmill center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$347
Average price / night
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Serene Retreat with Cove Views
Serene Retreat with Cove Views
Cottage
Eastham, MA, 02642, United States
0.8k from Jonathan Young Windmill center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$292
Average price / night
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Second Wind :039-O  An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24
Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24
House
Orleans, MA, 02653, United States
0.8k from Jonathan Young Windmill center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

10 Bedrooms24 Guests
10.0

Exceptional

14 reviews

$3170
Average price / night
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Recently Renovated Home Close to Nauset Beach and Downtown Orleans (2326)
Recently Renovated Home Close to Nauset Beach and Downtown Orleans (2326)
House
Orleans, MA, 02653, United States
0.9k from Jonathan Young Windmill center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
7.6

Good

5 reviews

$472
Average price / night
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Charming Waterfront Escape Along the Cove
Charming Waterfront Escape Along the Cove
Cottage
Eastham, MA, 02642, United States
0.9k from Jonathan Young Windmill center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$338
Average price / night
Check Availability
Peaceful Waterfront Cottage Escape
Peaceful Waterfront Cottage Escape
Cottage
Eastham, MA, 02642, United States
0.9k from Jonathan Young Windmill center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$355
Average price / night
Check Availability

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 Oceanfront Rentals in Jonathan Young Windmill.

Jonathan Young Windmill Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 657 verified oceanfront rentals in Jonathan Young Windmill. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Jonathan Young Windmill vary depending on the property size, exact beachfront location, and season. Rates typically start from around $257 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Jonathan Young Windmill offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Jonathan Young Windmill welcome pets. Currently, 33 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Jonathan Young Windmill often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.