
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 Bayđ¤hammock, hot tub, kayaksâ¤ď¸
With 180 degree water views, what could be better?! We saw birds, incredible sunrises over the bay, and enjoyed sunset in the hot tub. Itâs just right for a long weekend getaway to relax and unwind!

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 đon the beach. Stunning viewsđ
Love this cute cottage!! Perfect for a couples getaway and we were able to have our fur babies join us! Super clean, lovely views, the screened porch was perfect!!

Waterfront Gloucester Cottage w/ Private Boat Dock
This home was exactly what we needed - a beautiful, relaxing space with wonderful views. Every home along the private road is lovely - the azaleas in bloom during our April stay were stunning! The house itself was clean and had every amenity. The outdoor space was fantastic! We enjoyed our time sitting and rocking and looking at the river. We drove in to Williamsburg twice. It was a bit of a drive, but was worth it. Gloucester is a cute town and we did a little shopping & eating. Donât hesitate to book this home!

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
Richard was absolutely amazing and was so quick to respond when our trip changed and we were getting there a little bit earlier! We will definitely be coming back next year! The house stayed cold the beds were very comfortable and watching the sunset at the dock was by far my favorite thing!

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!

Waterfront Cottage w Hot Tub, Kayak, Fishing
We loved Marla & Willâs place. The house was clean, the kitchen had all the tools to prepare a meal, plenty of towels,comfy beds. The views were beautiful from the front porch, we used the kayaks and had my children play at the little beach that was available on low tide, my children played in the water, we only saw one jellyfish. We also did some fishing, used the crab trap, did not get any crabs but it was still a fun activity for my children ! We also found oysters in one of the beaches that appear on low tide. Also, we appreciated the storybooks for children, toys, bed rail guard and highchair. For grocery shopping we used Food Lion, the Little River seafood gourmet, and Jeff Country Market. We also ate at Reedville Market and it was delicious. Overall, it was a great stay and we canât wait to go back !
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
As serene as it gets (except Wednesday is the mowing day, but didnât bother us). Renee is super responsive, which helped a lot. The place is clean and very relaxing, it is remote though, any big city you want to drive to is 1.5-2hr drive. Had fun fishing from the dock, so many catfish there, anyone can catch. Friendly neighbors. Water is on the soft side. Fridge and cupboard had spices and condiments, and a water filter, which was a big plus. Pots and pans need replacing, thatâs probably the only negative. Would come back in a heartbeat. Thanks Renee and Ed!

"Bee Haven" Cottage Retreat
My parents and I stayed here for four days. It was the perfect peaceful getaway for us. The place was really cute, two bedrooms with queen size beds, a large bathroom, and the cutest kitchen-living room area. Gloucester is a sweet town to hang out in, and the host gave some great recommendations for local places to check out. Wonderful place, we will be coming back!!

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)
Lovely clean, everything needed provided cottage in a peaceful neighborhood with a short walk to the Bay. Kids loved the little beach and the sandbar when the tide went down. No bugs in April;)

The South Cottage at Vaux Hall Farm
What a truly special place Vaux Hall Farm is! The cottage and location couldnât be nicer. Thanks to Eric for the warm hospitality too!

TooFine Lakehouse, pet friendly waterfront cottage
The cabin was so beautiful! so clean and comfortable! the views were spectacular! one of the most relaxing vacations that we ever took! Thank you for sharing your wonderful cabin with us!!

Historic Ware River Cottage at Glebefield
The perfect spot for our Winter getaway. A beautiful setting and a well preserved colonial era cabin, perfect for exploring such an historic part of our Country. Quaint local restaurants, friendly people and a country setting handy to the lower tidewater Virginia. The icing on the cake was the fireplace for cozy evenings reading a good book. Sherri was a wonderful host! Sue and Marshall Rickert
Private cottage rentals

The Crab Shack
There is nothing more serene than waking up in the âcrab shackâ with the sunrise. What a comfortable and scenic spot. Even our dog, Juno, loved it! Took a sunset sail to celebrate a birthday and got front pier service! Our host, Carlisle, was extremely attentive and kind with any needs we had or hadnât thought of. Wish we had booked longer. We hope to return very soon!!

The Moore Cottage
The Moore Cottage is a perfect example of what the Chesapeake Bay has to offer, with beautiful views, kayaking, bird watching, swimming, and easy access to local markets. The house is a good size for a couple looking for a quite vacation. We plan on returning to enjoy this spot again.

Waterfront Urbanna Home w/ Private Dock & Pool
This house was a great place to stay. Everything was in perfect order and the location was excellent. I had one question during my stay and they were immediately available to help and were super friendly.

The Little House at Waveland
The Little House was a sweet and ideal getaway spot! The property is gorgeous, and the area of Deltaville and other surrounding towns are definitely worth the experience. Highly recommend!

Peaceful Haven: nature & charming town
Loved our stay, went there for a writers retreat and it was perfect, well appointed, clean and inviting. As a bonus in the later afternoon, with bikes provided at the cottage, we had a very nice afternoon ride, there were plenty of quiet roads to travel and their multi-use meadow is fantastic. Gita was very responsive to any questions and cordial. I will definitely return, look forward to it.

Waterfront Deltaville Cottage w/ Fire Pit!
We absolutely loved staying here! We brought our boat along, the marina is within walking distance and even though we got rained out, coming back to this house made our weekend stay well worth it.

Little Dipper -private beach,Kayaks & paddleboards
Wonderful place to stay with beautiful access to the river, I am so grateful I was able to spend my weekend here! Ned and Holly were responsive and everything was provided that I needed. Very kid-friendly so I hope to return with my toddler some day :)

Cottage on Prentice Creek, PA
I cannot find the words to express our families stay. When I say this was the best stay at an ABNB we have had thus far it was. The outside itself from the landscaping to the scenery was breathtaking. Checking in was a breeze. Once inside pictures cannot begin to show the beauty of this property. The hosts have really thought through a guest experience. They went over and beyond hosts duties adding extreme attention to details. Anything and everything you may need or want for your stay was there. Even with all the extra amenities and the beauty of the home our family instantly felt at home. We loved our stay so much we have already booked our next stay.
Destinations to explore
- Rentals with outdoor seating Middlesex County
- Rentals with beach access Middlesex County
- Kid-friendly rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with a firepit Middlesex County
- Rentals with pools Middlesex County
- House rentals Middlesex County
- Family-friendly rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Waterfront rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with lake access Middlesex County
- Beachfront rentals Middlesex County
- Rentals with a washer and dryer Middlesex County
- Rentals with a patio Middlesex County
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- Busch Gardens Williamsburg
- Buckroe Beach
- Kingsmill Resort
- Buckroe Beach and Park
- Grove Beach
- Grandview Beach
- Golden Horseshoe Golf Club
- Royal New Kent Golf Club
- Sarah Constant Beach Park
- Jamestown Settlement
- Water Country USA
- Cape Charles Beachfront
- Haven Beach
- Saint Jerome Beach
- Ragged Point Beach
- Langford Sand
- Kiptopeke Beach
- Outlook Beach
- Dog Beach
- Gloucester Point Beach Par
- Lane Beach
- Piney Point Beach
- Guard Shore
- Libby Hill Park