Windmill Point Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Windmill Point

Dining
Serenity on the Rappahannock

Serenity on the Rappahannock

White Stone
10.0 out of 10, Exceptional, (9)
"Clean; Beautiful views;Good bedroom to bathroom ratio;Well-appointed kitchen;Great water access;Quiet location;Easy check-in;Excellent communication with host."
United States
Carl H.
Serenity on the Rappahannock
On the beach, sun loungers, beach towels
Chesapeake Bay Beachfront Retreat

Chesapeake Bay Beachfront Retreat

White Stone
9.4 out of 10, Exceptional, (144)
"It was good except there were so many biting flies outside and no toilet papers and trash bags provided. Overall, was a great stay."
United States
Faith S.
Chesapeake Bay Beachfront Retreat
Exterior
Charming 2-bedroom house on the Chesapeake Bay

Charming 2-bedroom house on the Chesapeake Bay

White Stone
9.6 out of 10, Exceptional, (15)
"Wonderful time with the family and we had plenty of room. We loved learning about the history of the house. Would love to stay again "
United States
Wanda R.
Charming 2-bedroom house on the Chesapeake Bay
Property grounds
Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Grimstead
10.0 out of 10, Exceptional, (219)
"Everything you need is here, crab pots-caught a few blue crabs. Went fishing, we caught skate, croaker and an eel. 3 Kayaks, beach chairs, SUP , well stockedgrill, etc. "
United States
Kris K.
Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water
Outdoor dining
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

Diggs
$35 nightly
The price is $39
Dec 1 - Dec 2
Total with taxes and fees
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT
Exterior
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Irvington
9.6 out of 10, Exceptional, (172)
"We enjoyed our stay so close to the Tides Inn for the Taste of the Bay. Irvington is a quaint walkable town, perfect for getting away from the hustle and bustle of fast paced locations."
United States
Chris O.
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Fridge, microwave, oven, stovetop
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Reedville
9.8 out of 10, Exceptional, (10)
"We enjoyed our family vacation, so relaxing and accommodating. Loved the location and setup. "
United States
Tina h.
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed
Game room
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Reedville
9.8 out of 10, Exceptional, (61)
"Enjoyed the house, the view of the water, the dock, the crabs, the wifi, the quiet & location of the house."
United States
Arlene S.
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
3 bedrooms, memory foam beds, iron/ironing board, free WiFi
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

Hallieford
10.0 out of 10, Exceptional, (157)
"Peaceful setting wonderful views. Location is wonderful. Excellent!"
United States
Michael B.
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Exterior
Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront

2.0 star property
Mathews
10.0 out of 10, Exceptional, (22)
"Great location. Quite,clean, relaxing "
United States
Randy C.
$417 nightly
The price is $460
Nov 8 - Nov 9
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
Outdoor dining
Spacious waterfront home with dock and sunset view

Spacious waterfront home with dock and sunset view

Kilmarnock
9.6 out of 10, Exceptional, (12)
"We were attending a family reunion. Great to wake up and look out to see the water. So relaxing and serene. Just enough space to relax and unwind. I would however suggest to the owner to put some railings on the patio. We had a few seniors who need that extra support when stepping up. The grands loved fishing from the pier."
United States
Sneatha L.
Spacious waterfront home with dock and sunset view
Property grounds
The Little Blue Cottage - Topping : Waterfront!

The Little Blue Cottage - Topping : Waterfront!

Topping
9.8 out of 10, Exceptional, (50)
"Lovely place and attentive owner, felt right at home and will definitely return to this property for future trips to the area."
United States
Lory H.
The Little Blue Cottage - Topping : Waterfront!
Fridge, microwave, oven, stovetop
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Gloucester
10.0 out of 10, Exceptional, (175)
"Clean and well appointed cottage with beautiful views. The owners gave great recommendations for local spots to eat and have fun. Really enjoyed the stay. "
United States
Makayla L.
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg
Exterior
The Farm Overlook Treehouse At Blanchard Farm

The Farm Overlook Treehouse At Blanchard Farm

Diggs
10.0 out of 10, Exceptional, (1)
$105 nightly
The price is $116
Nov 10 - Nov 11
Total with taxes and fees
The Farm Overlook Treehouse At Blanchard Farm
On the beach, sun loungers
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Gwynn's Island
10.0 out of 10, Exceptional, (35)
"We have enjoyed 2 stays at the cottage. It is a wonderful location and the owners have been great and are very thoughtful. The beach is perfect, and we love the neighborhood. We can't wait to visit again!"
United States
karen w.
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
Outdoor dining
Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!

Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!

Irvington
10.0 out of 10, Exceptional, (303)
"Excellent property"
United States
Brock S.
Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!
Property grounds
Bubba Butler's Cottage

Bubba Butler's Cottage

Locust Hill
10.0 out of 10, Exceptional, (21)
"We had a fantastic stay. I could not have asked for better view of the river, and both sunsets and sunrises were perfect. It was a perfect place to unwind reading and writing. "
United States
Amy B.
Bubba Butler's Cottage
On the beach, sun loungers
Bay Front Small Contemporary

Bay Front Small Contemporary

Reedville
9.8 out of 10, Exceptional, (114)
"Absolutely love this place!"
United States
Robin S.
Bay Front Small Contemporary
Outdoor pool, a heated pool
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Reedville
9.6 out of 10, Exceptional, (95)
"We had a nice quiet week in this adorable and clean home just relaxing in the pool and spending time in the kayaks. We ventured out for some yummy Mexican food for dinner, ice cream in Reedville, and the nearby cafe to try their cappuccino and breakfasts but otherwise spent a nice family week playing games and swimming. "
United States
Judine K.
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Terrace/patio
Bayfront Escape, Private Dock, Large Deck, and Views!

Bayfront Escape, Private Dock, Large Deck, and Views!

Hudgins
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay at this property! The location was perfect- beautiful and peaceful right on the water. Dock was a great place to hang out at same with the cut-out beach areas. There is a great little restaurant nearby called hole-in-the-wall which had great food and the marina is just minutes away if you are looking to rent a boat or get out on the water.Overall, it was a fantastic stay and I would definitely recommend this home to anyone looking for a relaxing getaway in a quiet...
United States
Hoda P.
$380 nightly
The price is $420
Nov 24 - Nov 25
Total with taxes and fees
Bayfront Escape, Private Dock, Large Deck, and Views!
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.
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Top Windmill Point Hotel Reviews

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

10/10 Excellent
"Everything was great"
Larry 1-night trip
Posted 3 weeks ago
Holiday Inn Express Gloucester by IHG

Find out more about Windmill Point

Everything you need to know about Windmill Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windmill Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windmill Point vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windmill Point vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windmill Point. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windmill Point in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $39 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windmill Point rentals

At Expedia, we put the best Windmill Point vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windmill Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windmill Point vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windmill Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windmill Point?

Yes, there are vacation rentals close to the most popular local attractions in Windmill Point, or you can choose a more remote option if you're looking for relaxation.

What's the top vacation rental that Windmill Point has to offer?

Chesapeake Bay Beachfront Retreat: This highly rated vacation home rental in Windmill Point is located on the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Windmill Point is Charming 2-bedroom house on the Chesapeake Bay.

How many vacation rentals are there in Windmill Point?

Expedia has 13 vacation 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 Compass Entertainment Complex, or get outside and enjoy nature at Chesapeake Bay. White Stone Beach and Deltaville Marina are a couple of places you'll find in the larger area.

What are vacation rentals like in Windmill Point?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Windmill Point. Vacation rentals offer extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.