
Holiday rentals with outdoor seating in Essex County
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Top-rated Holiday Houses with Outdoor Seating in Essex County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

Beverly Beach House- Upper Deck
We stayed here for a week, and fell in love with it! The house has so much charm and character. We thoroughly enjoyed our stay, and want to stay there again. It was within walking distance to many places, including a beach. A definite charm in Beverly! The host was amazing! She was very responsive to our questions, and checked in a few times to see if we needed anything, which I appreciated. You are missing out if you don’t stay here!

Beach House on a Private Beach!
The stay was a lovely combination between relaxing and adventurous. My son thoroughly enjoyed a successful hunt for sea glass, while my husband and I were able to relax and enjoy the view in between adventures. Totally zen.

Master Suite with magnificent views of the ocean
We had a lovely long weekend at Natasha's gorgeous home. Spotlessly clean, with modern upgrades and appliances. The layout is a bit unusual as the house has been renovated and split into at least 2 units. Located on main road into Swampscott, with a view of the ocean (across the road) out the front windows--very beautiful even in the middle of winter! We had snow 2 out of 3 nights, and on the first of these there was a gentleman outside shoveling the driveway and back steps around noon. But by our check out time (noon) on Monday, nobody had cleared the snow. Got our car out ok, and we cleared off the back steps so we could bring our luggage out. There was conflicting info between the listing and what we were told by the owner re check-in and check out times--we messaged owner (twice) to clarify check out time and never heard back from her, so called her on check out morning--she apologized and honored the original listing. Info in owner's instruction booklet at house needs updating.

Hill House in Essex, Cape Ann
The home was cozy and well furnished. There was ample seating for our group to gather and relax in the charming living room. The home has been remodeled and redecorated reflecting a very strong sense of design. The kitchen is well stocked with cooking utensils and new appliances. The beds were super comfortable and the linens/pillows all very luxurious. Peter responds to messages very promptly and is extremely accommodating. We all loved Peter's home and hope we have the opportunity to return at some point in the future. It was a great place to celebrate 70 years of friendship!

Charming Home in Reading with a Large Yard
I recently stayed at Peter's place, and it was exactly as described in the posting. The pictures were accurate, and I was pleased to find the space clean and well-maintained upon arrival. The location is fantastic, as I grew up in the area. I truly couldn't have asked for a better experience. I wouldn’t hesitate to book again in the future. Highly recommend!

The House by the Sea
This was the PERFECT place for my family’s girls trip to Salem. It was only a 12 minute drive into town. The house is breathtaking!!! The pictures do not do it any justice. Everything is spotless and very welcoming. The private beach is a 3 minute walk up the road. The neighborhood is very peaceful and the neighbors were also very friendly. Tracy was an amazing host!!! 10/10 recommendation.

The Main Residence
From the moment we booked this property the host was communicating and super helpful! She gave us recommendations and also when we told her we were going to Salem she sent us the T station schedule and told us what line we needed to get on! The house was absolutely breathtaking! So comfortable and we felt so at home that we didn’t want to leave. So thankful we found this place and can’t wait to stay again!

Gloucester Beach House, near Good Harbor Beach!
Our stay at the Gloucester Beach House was great. It is a nice walk down to Good Harbor Beach, The Common Place Market and the neighborhood is peaceful. Its about a 10-minute drive to anywhere you want to go in Gloucester. Diane was responsive with any communication we had with her, and stayed in contact with us throughout the trip. We were grateful to be able to check in early after traveling all night to rest before beginning our trip adventures. For anyone interested, the Rhumb Line currently offers live music every night and its a variety of music. We went there several times and the musician's were top notch, and this is a place where the locals gather. We ended up visiting with friends and family and looking forward to another trip out to explore more of North Shore! Thank you so much for the wonderful home and stay.
Apartment rentals with outdoor seating

Stunning Union Square 2 bed/2 bath w/ shared patio
This was one of the best AirBNB that I've stayed at in a long time! Very clean and simply outfitted, which I really appreciate. Great location. Good communication. Cozy.

Two bedroom Apt with a deck
Rhona could not have been a more gracious host! We were traveling back east for the holidays and needed a place to stay. In addition to the many treats she left for us, she bought a little Christmas tree! The apartment is perfect with everything you could ever need or want. We could walk to stores and restaurants. If we had questions she was very responsive. Marblehead is a beautiful town. I highly recommend a visit to Rhona’s AirBnB!!

Harborside Oasis | Harbor View | Heart of Downtown
This is a beautiful apartment located in the heart of Rockport. Will definitely come back here if possible for another trip!

Newly Renovated Ocean View 2 Bdrm Apt
Visiting a large family for Thanksgiving can always be hectic but staying at Anna's and Milan's house provided that 'calm base camp' it is always nice to come home too. Since the T stops literally at the front door you really don't need a car. But if you do have one there is parking spot in the driveway so what more can you ask for in Boston in regards to transportation. The view is beautiful from the second floor apartment and I literally only had to go across the street to gather my most important collectible on each trip, native beach stones. there's no better place to stay in Winthrop

Amazing Ocean View In-Law Apt.
Susan’s place was stunning. I grew up close to this area so I knew what to expect, but in all honesty, the back yard was still a bit unreal. You can’t beat open ocean views, a hammock, and sitting area, and a porch/deck with levels leading down to the ocean. The space itself was more than enough room, very clean and comfortable. We had everything we needed and our young son had the space to enjoy himself. We would definitely book with Susan again!

Ocean Wave unit, Melo's Beach House Rentals
We came in from out of town for a few days and were so pleased with our stay. The house was clean and comfortable. It was very close to the beach and walkable to the center for entertainment and restaurants. We would absolutely book again. Thank you for a wonderful weekend.

Oceanfront Pool. Close to Boston. Free Parking.
Carol and John’s home is a hidden gem! It is located right on the beach and you can wake up every morning to the most beautiful sight. My husband and I wanted to go away from the weekend but not have to travel too far. This was the perfect place to allow us to relax and unwind for an extended weekend. The hot tub and fire place made everything even better! We’ll certainly be back! :)

Cambridge Retreat - Sunny 2BR - Close to Harvard
Shelley's place in Cambridge was the best I've stayed in Boston yet. Such a charming, lovely home surrounded by beautiful older homes in a walkable neighborhood. The best parts were the natural light and the beautiful way that Shelley has it decorated- very classy and eclectic. Comfy furniture, comfortable beds (even the sofa bed in the guest room!) There were even snacks and drinks left for us which was so nice. We'll definitely be staying here again!
Condo rentals with outdoor seating

A Cozy 3 Bedroom Home Close To Boston & Parking
Had a nice time staying at Shirley's place - it's a quick walk to multiple restaurants and coffee shops and was a comfortable home base for visiting friends all over Boston.

Luxury 2 Bed, 2 Bath, Plus Loft, Modern Condo
Our family really enjoyed our long weekend at Donald’s place. The location is great, right in the middle of Marblehead, walkable to old town and the various shops and restaurants that dot the area— a great base for visiting friends and family on the north shore. We’ll definitely look to stay here again if available the next time we’re in the area.

Bright & Spacious Home in Davis Sq, Somerville
Cayla’s place was perfect for us to visit our family in Somerville - location, parking, and amenities. Recommendations for restaurants and activities provided. Comfortable beds and furniture. Well stocked kitchen. Cayla was incredibly responsive. Will stay again if available.

My Place - 2 Bedroom Condo with Parking
Kelly was an excellent host. My friend and I were visiting friends in Salem. The house was perfect for our needs in a quiet neighbourhood. We had everything we needed. Clean and Quiet I would highly recommend. Thank you!

Bearskin Neck Rockport ★ Amazing Views ★ Parking
Christina's property was a wonderful place to escape to for a few days! It is the perfect size for 1-2 people, has everything you need, and the view is unbeatable. The parking space is incredibly convenient and the location of the property provides easy access to the rest of Bearskin Neck and Rockport proper. I hope to stay here again in the future!

The Salem Porch House
I took my wife to Salem for her 40th birthday and Alex's place stood out when I was looking for a place to stay. Her room had all of the amenities we were looking for and was conveniently located in downtown Salem. Alex was very responsive and helped us find fun things to do during our trip. Highly recommended.

Boston 2Bd Kg&Qn - Harvard MIT Subway w/parking -2
Enjoyed our stay; perfect location. When I had questions regarding the heater, I texted through the app and was immediately contacted for help/instruction. Very appreciative of fast response. House very clean, kitchen fully stocked.

Samuel Tucker House - Downtown Luxury 2 Bed Condo
Brian’s place was proximate to everything we could’ve possibly needed for our post-Christmas New England trip to visit family. The home was clean, tidy, and well-stocked with the essentials. The layout made it feel spacious, which is great when traveling with our 3-year-old, and Brian’s local recommendations were spot on. Would absolutely stay again.
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- Hampton Beach
- Wells Beach
- Boston Common
- TD Garden
- Fenway Park
- North Hampton Beach
- Harvard University
- Ogunquit Playhouse
- Long Beach
- New England Aquarium
- Long Sands Beach
- Prudential Center
- Museum of Fine Arts, Boston
- Symphony Hall
- Hampton Beach State Park
- Isabella Stewart Gardner Museum
- Bear Brook State Park
- Aaronap Cellars
- Ashland State Park
- Boundless Adventures Zipline and Aerial Park
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Hopkinton State Park
- Cochituate State Park
- Great Brook Farm State Park
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