
Cottage vacation rentals in Middlesex County
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Top-rated cottage rentals in Middlesex County
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Popular amenities for Middlesex County cottage rentals
Cottage rentals with a hot tub

Private point on the Bay🌤hammock, hot tub, kayaks❤️
They were amazing hosts, the place and the views were phenomenal and all the toys and kayaks were a great addition to the stay. The pay attention to the small details that make the trips great and we can’t wait to return.

The Cottage @ Captain Genes - Secluded Waterfront
Our stay in this home was such a treat! We enjoyed utilizing the kayaks to boat around in Chesapeake Bay. The hot tub was an absolute delight, perfect for evening stargazing, saw lots of shooting stars, and could see the water of the bay from the hot tub. We also enjoyed doing November cold plunges from the hot tub to the pool. While the living room is not expansive, it fit our needs for family game & movie nights. The bed linens were so comfortable, and Lori was beautifully responsive & friendly when we would reach out with a question. We also enjoyed the nearby Sandy beaches.

Bay cottage 🏖on the beach. Stunning views🏝
We LOVED our stay! The screened porch overlooking the beach was so peaceful and our favorite place to be in the evening. The house was lovely, well cared for, very clean, and very tastefully decorated. The welcome book provided everything you needed to know about the house and surrounding area. We will be back again!

Waterfront Gloucester Cottage w/ Private Boat Dock
We had a great time staying here! Clean, modern, fully stocked home just as described in the listing and photos. The sunsets over the water are indescribable. Relaxing hot tub, wonderful outdoor space, lovely campfires, and comfortable bed and bath rooms made our trip stress free and extremely enjoyable. We barely left the property - we felt right at home. Our point of contact host, Ana, was very responsive and communicative. Would definitely recommend! Look forward to booking again in the future! Thank you for a vibey holiday weekend!

Bungalow w/ Large Yard: 8 Mi to Cape Charles Beach
We absolutely loved staying here! It was the perfect distance from Cape Charles where we visited during the day. It was the perfect little getaway!

Waterfront Heathsville Cottage w/ Dock & Hot Tub!
This is a really nice getaway that is peaceful and serene. The home is older, but has some nice updates. I am one that appreciates a home with character. It is in a secluded area, so at night its gets really dark in the hot tub area which we made good use of. Waking up to views of the lake was my favorite part of the day. I was sad when the sun started to go down. There are neighbors, but the houses aren't very close to each other. It is located in a small town so there aren't many food options. The restaurant we went to wasn't very good, so I'd highly recommend cooking for your stay or bringing food. That's what we did. We cooked our meals and grilled. It was fantastic. Four of us stayed there comfortably. Two couples. Overall we had a nice 3 days and I'd highly recommend.

Old Log Cabin School House w/10 acres on the Bay
This old log cabin school house, this was one of the most amazing experiences our family has ever had in an Airbnb. The history in this home is something like I’ve never witnessed before in my life. You can feel the love that has been poured into this unique stay. It felt like home with endless bonuses found throughout the home, carriage house and property. Richard was an incredible host and this was by far the most personable experience we have ever had in all our years using Airbnb. You can feel the peacefulness this place offers from the moment you turn onto the driveway. The sunsets are breathtaking and we saw deer, turkey and a ton of other wildlife daily. One night right after sunset my husband caught a 24” speckled trout! Our four children, ages 12, 9, 4 and 1, all had a blast. We brought a baby gate for the living room/kitchen doorways and it was perfect! Downtown Mathews is adorable and we loved the visitor center. Definitely check this place out if you have the opportunity ?

3 BR Bay Home w Private Dock & all the Amenities
Our trip to The Half Shell Haven was great! The place was clean, extremely well stocked, and included many extras! We had crazy weather the first two days, but we had plenty to do at the house. My boys loved being on the water and the game room and my daughter loved the hot tub and bicycling. My daughters service dog enjoyed a nice reprieve and seemed so happy. We had a great time, and were honestly sad to go! If we find ourselves back up in Virginia we will definitely stay here! Thank you for the care and attention to detail to ensure a great trip!
Pet-friendly cottage rentals

ESVA Down by the Sea & Pet Friendly
This place was perfect for what we were looking for! We will certainly be booking again when we come back.

Modern 2 Bdrm Cottage in Historic River Community
Perfect getaway for rest, relaxation and fun! Kayaks were fun, too breezy and chilly waters for paddle boarding, maybe next time! Beautiful location! Clean and comfortable, felt like home!

"Bee Haven" Cottage Retreat
I had a great stay! The space was quiet, and very clean—perfect for relaxing. It was also pet-friendly, which was a big plus. The host was friendly and communicative, making everything easy from check-in to check-out. Would definitely stay again!

A "True" Chesapeake Bay Waterfront Experience!
I truly wish I could put into words just how beautiful and peaceful this home and property were. It is truly a place that was so inviting and well maintained it made me miss the eastern shore of Virginia and start looking at properties in the area. The land is so cool to walk and explore and the bay at this home is just serene. To be able to wake up and see the view this home has is just spectacular. Matt is spot on with the description of his home and you truly can't find one thing wrong with this home or the property surrounding it and having a dog,it is so key with the wash station outside because our lab puppy could not get enough of the bay or going out in the kayaks with us. I truly wish they had more stars to rate this home. Thank you for being so gracious and allowing us to visit your spectacular home!

Cottage by the bay (private peaceful surroundings)
Great experience and lovely host.

The South Cottage at Vaux Hall Farm
What a truly special place Vaux Hall Farm is! The cottage and location couldn’t be nicer. Thanks to Eric for the warm hospitality too!

Sunset Haven
This is our second time staying at Sunset Haven— appropriately named. Gorgeous sunsets and weather was perfect. Great and considerate communication with Terri. House was pristine and had every thing you could need. We will be back! Thank you Terri!

TooFine Lakehouse, pet friendly waterfront cottage
We had a wonderful time! The atmosphere was incredibly peaceful and relaxing—perfect for unwinding, even on the rainy days we had. The space was beautiful, cozy and calm. Gina was a great host—very responsive and proactive in checking in to make sure everything was going well.
Private cottage rentals

The Crab Shack
My husband and I loved our stay at the Crab Shack! It was convenient for our weekend plans and we loved having direct water/dock access.

The Moore Cottage
The cottage was better than we could have imagined, the pictures don’t do it justice. We took full advantage of the backyard views while having breakfast on the back deck. A quick drive to the surrounding towns provided plenty of dining and entertainment options. Windmill Point Marina was a 5 minute ride with live music and good eats. We enjoyed the Northern Neck and look forward to our next stay.

Locklies Innlet, A unique waterfront experience!
What a perfect cottage! Beautifully (but comfortably) furnished, right on the water, incredibly well-stocked. Arranged so families can spread out, or gather together. Everything you could possibly require or desire for a vacation or getaway was there. And the area is full of things to do--walks, birdwatching, antiquing, or, if you're an architecture geek like me, historic sites and buildings. You're also a 3-minute walk from the best restaurant on the Northern Neck, Merroir Tasting Room. Can't wait to come back.

The Little House at Waveland
The hosting family couldn't have been any more friendly and the house was lovely and in a wonderful neighborhood.

Peaceful Haven: nature & charming town
What a wonderful place and host! Pictures do not do it justice. It looks like a cosy cottage on the outside, but it is much bigger on the inside. Very clean. The first floor provides an extremely functional living space - living room, dinning area, kitchen and sun room. The couch in the sun room is extremely comfortable. The bedroom and bathroom upstairs are palatial. The two bedrooms downstairs are very cosy and have their own beautiful bathrooms. One of the downstairs bedrooms has a wonderfully enclosed porch off of it. Everything is up to date and very functional - Wi-Fi, heating and air conditioning, washer & drier, kitchen appliances, etc. And the host was quick to respond to any questions. We hope to return soon and take advantage of the outdoor activities.

Unique & bright two-bedroom waterfront cottage
We had a wonderful stay! The house is immaculate and well taken care of with everything you need for a comfortable stay including great local recommendations. We enjoyed watching a beautiful sunset sky while relaxing on the deck. It was a very easy check-in/check-out. Would return and would recommend. Thanks for a great stay!

Irvington Cottage - Vineyard Birdhouse
We had a wonderful stay! We have stayed at this Airbnb a few times and it is always perfect! Thanks so much!!

Little Dipper -private beach,Kayaks & paddleboards
We loved our stay at the Little Dipper. The house is spacious and comfy - exactly as advertised. It is well-stocked yet neat and clean with no clutter. The screened-in porch is a real gem that connects to a boardwalk leading to a river-view deck. Whether home basing to travel, or tide-watching and kayaking, the Little Dipper's location and setting facilitates a relaxing stay with stunning view day and night. The general location is also super. Urbanna, VA is a quaint little town and you're not far from historic Yorktown or Williamsburg. If you are staying in this vicinity, the Little Dipper is a win. We would stay here again.
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- Chesapeake Bay
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