
Guesthouse vacation rentals in Middlesex County
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Top-rated guesthouse rentals in Middlesex County
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Popular amenities for Middlesex County guesthouse rentals
Family-friendly guest house rentals

Fully Renovated, Ocean Views, Fireplace & Beach
Dawn’s place is private, well-appointed and in a fantastic location. You have an ocean view from the cottage, have access to a small semi-private beach, and a brief walk along the coast via the gorgeous neighborhood takes you to the larger Ocean Beach & boardwalk. Additionally there are very good restaurants, state parks, museums and pubs nearby. You’ll feel pampered by Dawn’s consideration and attention to detail and refreshed by the location and beaches.

Chic Coastal Retreat: Modern Apt Steps from Beach
Nice ground floor apartment across the street from the beach and 2 blocks from the state park. Love the outdoors. And Delores and her brother were amazing. Friendly, responsive, and helpful.

Montauk Heaven, Beach & Woods
Christine was an awesome host. We felt right at home and the place is a nice 15 min walk from the beach (or an even shorter drive). The house is beautiful and it felt personal and warm!

Beautiful Airy Barn in Springs
Staying at Gillian’s place was amazing! It was very peaceful and tranquil and not too far from Main Street where we could shop and eat. The barn is quaint and homey and sits beautifully on a lawn. We loved our stay and will be returning in the future!

Farmington River Carriage House Pleasant Valley CT
Great stay! Lots of wildlife on the river. Will definitely come back.

House on Little River / Writer Retreat
Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!

Quiet studio with sleeping loft and deck
I will book again and again. The comfort of the bed and shower was fantastic. The appliances were updated and I will recommend this little piece of solitude Heaven. It’s like a wee nature refuge and Perfect location. The hosts were attentive and kind. A million thanks!

Waterfront carriage house studio
John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!
Guest house rentals with a patio

Private Luxe Cottage at Gates of Wine Country
We had a wonderful stay at Carrie’s listing. When we first arrived, Carrie was still cleaning up so we were invited inside for a cup of wine. The airbnb had almost everything we needed (minus a microwave) and the property had super friendly chickens and every amenity needed for a stay-at-home vacation. Carrie was even kind enough to have us stay a little past check in to finish some work meetings. We appreciated everything and would recommend this to anyone coming to North Fork :)

Private guesthouse
Stayed here last November with a friend and was so glad I booked again! The place was clean, comfortable, and exactly as described. The host was responsive and made everything easy. Great location, too. Will definitely book again!

Brand new & close to casinos with HOT TUB
Beautiful and peaceful. Perfect place to stay to get out of town for a day. Highly recommended

Central Hamptons Guesthouse
The Central Hamptons Guesthouse was a wonderful stay - it's a great location and a really charming house. Michael was a very communicative host, and overall it was a seamless, easy, relaxing weekend.

Hill Coast Cottage: Freshly Renovated
The pictures really don’t do it justice , the place is adorable. The kitchen has all new appliances, and it has every amenity you could need for a long or short stay.

Cottage in Quiet Corner. Four miles from town.
We loved our stay with Gary and Cindy! Cindy met us and showed us around. She kindly offered books for our kids and showed us her beautiful plants. They have lots of grandkids so they were happy to let our kids run free in their yard with their dogs, which my kids loved. The kids loved the little cubby hole beds and the cottage was comfortable and cozy. Cindy even had muffins and flowers awaiting us in the cottage. Highly recommend!

New Haven Pizza Cozy Guest House 1 mile to yale
I had a very peaceful stay. The area was quiet and as a light sleeper, I appreciated that. The decor was attractive and I loved the subway tile, sunken kitchen sink, and beautiful counter top. Everything worked fine and the hosts were easy to reach. There’s a nice organic market about three minutes walk away with good prices; it was so convenient to pick up a few groceries. I also appreciated the parking spot right in front of entry door! I definitely recommend this place!

North Country Cottage
Wonderful place to stay in wading river! Hosts were excellent and their place was cozy. Recommend to anyone needing a place to stay in the area.
Guest house rentals with a washer and dryer

Camellia Springs - Solace & Rest
I stayed at Camellia Springs across three days and really enjoyed the space, but Camille is what makes the place extra special. She had great communication and made sure my check-in went smoothly including a tour of some of the features and local suggestions. She also double checked I had everything I needed throughout my stay. I got the impression she wanted me to feel at home. The space itself is great on its own. The bathroom is spacious and there’s a separate mirrored space besides the sink itself that’s like a makeup vanity. The toilet is at the far end of the bathroom tucked around a corner so it’s definitely set up for multiple people to be getting ready without feeling crowded. The shower also has good pressure without being stingingly sharp. The open living space between the living room and kitchen makes for a great hangout. Overall, if I could find a space like this with a host like Camille in all my travel locations, I’d choose it every time.

Stylish Studio Suite on Shelter Island
Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!

Southold- Adorable 1 Bedroom Cottage
Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.

2 Bedroom Hamptons Waterfront Cottage Rental
A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.

Square 6ix
My folks have stayed here a few times while visiting me and the family, and it's been great every time.

Waterfront Cottage on the Niantic River
We had a wonderful time. The weather cooperated a couple of days so that we were able to have dinner on the deck overlooking the Niantic River. A big bonus was that we were within walking distance from the friend we were visiting. Matt was very friendly and helpful. The bed was comfortable. The kitchen was nicely stocked with dishes, utensils, etc. The starter coffee pods were a nice touch. The bathrooms were clean and spacious. We would definitely stay here again.

Southampton Village - Escape to Tranquility
Southampton is just expensive so value is hard to judge. The pool is amazing. The home is a mix of old and new, but very comfortable. Beach is about 1.5 miles away and town just a little less.

Perfect guest house very private
Don‘s place was spotless and private. Don himself was very easy to communicate with and responded almost immediately. We were happy to stay at his place and visit nearby relatives. We would recommend Don‘s place to anyone wanting a lovely, private and spotless place to stay.
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Six Flags New England
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- Seaside Beach
- Jennings Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Shennecossett Beach
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- The Connecticut Golf Club
- Burwells Beach