Windmill Point Holiday Rentals

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Holiday Rentals in Windmill Point

Exterior
Charming cottage across the picturesque shores of Little Bay
9.6 out of 10, Exceptional, (15)
"Thoroughly enjoyed our stay at the house and venturing around the area."
Charming cottage across the picturesque shores of Little Bay
Outdoor spa tub
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (39)
"Everything you want to do is right there at the house..Fishing, crabbing. Canoeing, kayaking and so much more. Already planning a trip back this summer."
Enjoy family fun and Sunsets at Piankatank Point.
Property grounds
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (62)
"Nice"
Oceanfront White Stone Cottage w/ Private Beach!
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Fridge, microwave, stovetop, dishwasher
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (8)
"Very accommodating, comfy beds (a real +). Kitchen fully loaded with supplies (including spices and condiments). We spent so much time down on the dock crabbing and fishing. Our dogs loved the freedom and space. Made friends with others in the area and did dog walks with them."
Waterfront Reedville Home w/ Private Dock!
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (113)
"Pet friendly well kept property with more amenities than others we’ve stayed in when it comes to outdoor activities, kitchen supplies/gadgets to the outdoor dog bowl. Quiet and private location with nice views from porches and even inside. We enjoyed our stay and so did our pups. 1 day with bad weather and it didn’t matter we had movie marathon and a great view. Some hunting dogs would come visit and make our girls wonder further than normal but zero complaints otherwise. Premium beds and...
Private, 7-acre waterfront retreat on Winter Harbor Haven
Property grounds
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
9.6 out of 10, Exceptional, (14)
"Cannot beat this location. The private beach was just incredible. We came with two dogs who enjoyed going for a swim each morning. The kids loved hanging out on the beach all day. The hosts were responsive and thoughtful. When we arrived the first night the lights were on and music was gently playing. Thoughtful touches that were very much appreciated. We could not have hoped for a better experience."
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
Sun-loungers
Room on river with sunset views and private beach!
10.0 out of 10, Exceptional, (17)
"Lovely"
Room on river with sunset views and private beach!
Fridge, microwave, oven, stovetop
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (62)
"Seriously, don't think twice about booking this property! It's in a beautiful, quiet setting and about an hour drive from countless attractions. We went to Williamsburg, short 45 minute drive through beautiful country. The property is exceptional! The host has thought of literally everything and well appointed. Looking forward to returning soon!"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Fridge, microwave, oven, stovetop
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (13)
"Our stay was great! The host gave us all the information we needed, and the property was amazing. We spent plenty of time talking and reading out on the water while enjoying the view. This property is quiet and fairly secluded but also doesn't feel far from food and entertainment. We loved our stay and would recommend this location to anyone!"
The price is NZ$508
per night
3 Jun - 4 Jun
Welcome to this Waterfront Home with Amazing Views
Property grounds
Tranquil River House w/ Grill & Views, Near Town!
9.8 out of 10, Exceptional, (12)
"This was a great place for our family to gather. We have been visiting family in the area for almost 20 years and our own family has out grown the guest rooms at the in-laws sending us in search for a bigger place to stay. We have stayed in several rentals in the past 5 years and this is the first one that we really want to return to. The view of the sunsets from the sunroom are breathtaking. The neighborhood is quiet with plenty of space between the houses. We had enough space for us, the 3...
Tranquil River House w/ Grill & Views, Near Town!
Property grounds
Waterfront Hartfield Vacation Rental w/ Dock!
9.8 out of 10, Exceptional, (9)
"Absolutely loved this place. Quiet, secluded and so relaxing. We enjoyed the view and listening to nature. Owner was wonderful. I highly recommend staying here."
Waterfront Hartfield Vacation Rental w/ Dock!
Aerial view
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
9.6 out of 10, Exceptional, (37)
"Had a great stay, with little to no complaints!"
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
Property grounds
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
10.0 out of 10, Exceptional, (179)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
Interior
Amazing views of the Chesapeake Bay.
10.0 out of 10, Exceptional, (11)
"We were in town for a reunion with good friends and former neighbors. This cottage was perfect for our needs! Spacious and comfortable. Kitchen stocked with everything you might need. Great view of the river and a covered front porch to sit and enjoy it! Lovely area to walk around as well. Host very responsive! I would definitely stay here again. Highly recommend!"
Amazing views of the Chesapeake Bay.
Beach nearby
Cozy cottage on the Chesapeake Bay
10.0 out of 10, Exceptional, (26)
"What a sweet place to stay. Perfect for a nice relaxing weekend ."
Cozy cottage on the Chesapeake Bay
Exterior
Tranquility on the Water! Renovated Modern Farmhouse on Private Cove on N. River
9.8 out of 10, Exceptional, (62)
"I met up with a good friend for a long weekend that immediately felt too short. The house is absolutely wonderful! Views galore. Total peace and tranquility. Very private. We just wanted to enjoy the cove, drink coffee by the water and enjoy excursions to Gloucester, Gwynn Island, and Mathews. The house was perfectly located but was wonderful just one its own. We hope to come back soon and take out the kayaks in the warmer weather."
Tranquility on the Water! Renovated Modern Farmhouse on Private Cove on N. River
Property grounds
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (242)
"Cute cabin. Porch was perfect in the morning. Listening to the birds while drinking coffee was relaxing. Location was perfect as we have family in Onemo. It was a relaxing & perfect."
Historic Cottage on Ware River Estate
Private kitchen
Monthly discount- beautiful house, Gloucester VA
10.0 out of 10, Exceptional, (13)
"We visit the area a lot to see family so I've stayed in quite a few rentals here. This is my first time at this property and I would stay again. Looks just like the listing. I appreciate the simple layout for our needs. 3 bedrooms meant we were comfortable at night. I thought the one king bed was pretty soft and the other firm; both comfy just think that's helpful to some to know. The living area and kitchen/dining space aren't huge but again you should know that from the pictures and it worked...
Monthly discount- beautiful house, Gloucester VA
Property grounds
The Little Blue Cottage - Topping : Waterfront!
9.8 out of 10, Exceptional, (29)
"Little blue cottage was perfect. We wouldn’t change a thing. So nicely appointed and such a beautiful location."
The Little Blue Cottage - Topping : Waterfront!
Property grounds
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
10.0 out of 10, Exceptional, (23)
"Situated on a point with water on two sides of the expansive property, the setting was amazing. The house is a mid-century ranch that has been thoroughly updated. We had lousy weather, so we did not get to enjoy the large water-side deck and firepit, but even the indoor views of the water from the kitchen-den area were wonderful."
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Don't see what you're looking for?
See all available properties in Windmill Point
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Windmill Point you may be interested in

Exterior
Charming cottage across the picturesque shores of Little Bay
9.6 out of 10, Exceptional, (15)
"Thoroughly enjoyed our stay at the house and venturing around the area."
Charming cottage across the picturesque shores of Little Bay
Exterior
Holiday Inn Express Gloucester, an IHG Hotel
3.5 star property
7.2 out of 10, Good, (512)
"Nice people great place very clean"
The price is NZ$206
per night
9 Jun - 10 Jun
Holiday Inn Express Gloucester, an IHG Hotel
Exterior
The Tides Inn
4.0 star property
8.8 out of 10, Excellent, (139)
"I can’t wait to visit again when the renovations are completed."
The price is NZ$709
per night
2 Jun - 3 Jun
The Tides Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windmill Point holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windmill Point. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windmill Point. Seeing all the best attractions is bound to make you fall in love with Windmill Point. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windmill Point short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Windmill Point?

Yes, there are holiday rentals close to the most popular sights in Windmill Point, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windmill Point has to offer?

Waterfront Reedville Home w/ Private Dock!: This holiday home rental outside of Windmill Point is located on the waterfront, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Windmill Point?

Expedia has 12 holiday rentals for your stay in Windmill Point.

What can I see and do in Windmill Point?

While exploring the area, visit family-friendly sights like Deltaville Maritime Museum, or get outside and enjoy nature at White Stone Beach. Deltaville Marina and Gwynn's Island Musuem are a couple of places you'll find in the wider area.

What are holiday rentals like in Windmill Point?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windmill Point. Holiday rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.

Recent reviews of Windmill Point properties
Expedia verified reviews