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

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202 Beach Home Rentals in Jonathan Young Windmill (Starting from $257)

Town Cove Oyster House
Town Cove Oyster House
House
Eastham, MA, USA
0.2k from Jonathan Young Windmill center

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

3 Bedrooms6 Guests
7.0

Good

1 reviews

$698
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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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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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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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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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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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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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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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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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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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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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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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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 Luxury Waterfront Home with Pool and Dock  NEW 5% Discount Until Feb. 28th
Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th
House
eastham, MA, 02642, United States
0.4k from Jonathan Young Windmill center

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

4 Bedrooms10 Guests
10.0

Exceptional

33 reviews

$1554
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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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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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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NEW Luxury Waterfront - Hot tub, Sauna, Game Room
NEW Luxury Waterfront - Hot tub, Sauna, Game Room
House
Eastham, MA, 02642, United States
0.8k from Jonathan Young Windmill center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
New to Booking
$1290
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
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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
Peaceful Covefront Cottage Retreat in Eastham
Peaceful Covefront Cottage Retreat in Eastham
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
$346
Average price / night
Check Availability
Walk to Water, Cozy, Dog Friendly!
Walk to Water, Cozy, Dog Friendly!
House
Orleans, MA, 02653, United States
0.9k from Jonathan Young Windmill center

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

3 Bedrooms8 Guests
New to Booking
$482
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 Beach Rentals in Jonathan Young Windmill.

Jonathan Young Windmill Beach Rentals on the Map

Frequently Asked Questions

You can explore 202 verified beach rentals in Jonathan Young Windmill. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Jonathan Young Windmill vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $257 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Jonathan Young Windmill offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Jonathan Young Windmill welcome pets. Currently, 26 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Jonathan Young Windmill often include amenities designed for coastal living, such as Ocean View, Fireplace/Heating, and View. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.