Holiday rentals with outdoor seating in Massachusetts

Serene and charming riverfront hideaway. In a residential neighborhood but very quiet. You are 5-10 minutes from great restaurants, shopping, Dennis Beach but it all feels very secluded. We went kayaking every day from the private dock, saw swans, sea lions, and hawks. The space is clean, boho-chic, very comfortable beds, easy to use gas fireplaces. Primary bedroom sitting area/sunroom is dreamy for reading. Kitchen has everything you need. We thought we might miss an ocean/bay view but we didn't at all. Very reasonably priced for the quality. Meg replied to all messages within minutes. We would absolutely come back. Great for a couple or small family.

Jennifer‘s place was the perfect homebase for a week of vacation, exploring Cape Cod and even venturing up to Boston and Salem. Her restaurant recommendations were helpful and spot on. Our favorite was the Black Whale in New Bedford. Comfortable beds, beautiful new appliances in the kitchen, and the soaker tub in the upstairs bath was so fantastic. It was nice to come home to such a quiet, peaceful place after a day of adventuring. Jennifer was super responsive and made our stay easy and delightful. One of our favorite excursions was to the boardwalk and beach and sandwich. We hope to come back someday to keep exploring all of the cool things in Massachusetts.

From the moment we arrived, we felt completely at home thanks to the incredibly warm and welcoming hosts, Tania and Glenn. They went above and beyond to make our stay comfortable, offering great local tips and always greeting us with a smile. Their hospitality truly made a difference. The home itself is absolutely stunning—beautifully designed, impeccably clean, and filled with thoughtful touches that made it feel extra special. Whether we were enjoying a quiet morning coffee or relaxing in the cozy living area after a day of exploring, everything was perfect. This was one of the best Airbnb experiences we've ever had. If you're lucky enough to find availability here—book it! You won't regret it. Thank you, Tania and Glenn, for a truly unforgettable stay! 💛

We had a great time here. Loved the cozy cabin. Great views of the pond! Would definitely stay again.

Lauren was an excellent host! Cottage is absolutely beautiful! Felt right at home , she was very responsive and very helpful. This place has all the amenities, perfectly located for everything we had planned .

Great location right on the lake with waterfront access right off the back deck! The house was very clean and offered a great view of a calm lake. Area was quiet but, with the windows open, highway was audible but definitely not a deal breaker. Kitchen was amazing and overall the house was very clean. Highly recommend for anyone looking for a getaway with lake access and a great spot to fish. Little ones caught plenty of fish and with great weather, the property was enjoyed to its entirety. Be advised: there is a resident that lives above the garage so the parking in the driveway is shared. Do not be alarmed because we did not see the resident at all during our 5 day stay. Host was responsive and offered a great location for the family to enjoy.

Gary’s home is beautiful. We especially enjoyed the covered porch and Adirondack chairs that overlooked the water. The house was spotless both inside and out! The kitchen is well stocked with everything that you will need to prepare a meal. Thank you for sharing your home Gary!

We cannot praise Mimi and Manny highly enough. The place was beautiful, with every amenity needed to feel at home. Our hosts were friendly, responsive, and charming. They went out of their way to make us feel welcome and comfortable. The unit was spacious, clean, easy to find, easy to check in, and peaceful. We particularly enjoyed the front porch. We stayed for three nights, and our every need was met. Highly recommend both the place, and the hosts, for anyone needing to stay in the area.

Our experience at Carrie's studio apartment was just what we needed after a busy day attending to a family project. The apartment is spacious and nicely appointed with a comfortable bed, couches and lounging chair. The kitchen is well-equipped and the bathroom neat and clean. Although we didn't have much time to enjoy it, a small outside porch overlooking a lower garden and an expanse of a neighbor's green lawn was an added perk. The apartment is a short walk into the village of Shelburne Falls with its diverse shops, many eateries, pharmacy (good spot for an ice cream soda), small grocery store (an organic oriented store is just across the bridge), bookstore, and very nice wine store (near the Pot Holes). Don't miss Gypsy Apple, a culinary treat for a special occasion (check for the evenings open as they are limited). Our respite at Carrie's was peacefully quiet and restorative. I have no reservations about recommending Carrie's lodging.

Look no more! Winter Island Retreat is a seaside oasis that creates an atmosphere of tranquility and peace. From the moment I arrived I was struck by it's beauty captivated by the stunning sunrises to start each day The retreat is charming and a place of solace. The beautifully manicured lawn and gardens filled with lush floral designs adds to its magic. while the front porch with its rocking chairs, invite you to slow down and savor your morning coffee or lose yourself in a good book. Evenings are equally special walking the path to the beach and settling into the adriondack chair with a glass of wine It's a peaceful ritual that grounds you in gratitude. The home itself is cozy, comfortable and thoughtfully decorated with calming beachy touches that make you feel at ease. It's perfectly located just minutes from downtown Salem. I'm grateful to be one of the lucky guests to stay in David's home. He was a kind and gracious host. A truly memorable retreat I will be back

We had a fantastic stay at this place! The house was spotless, with a fully stocked kitchen and bathroom that made everything super convenient. Thiago was incredibly helpful, attentive, and kind throughout our stay, which made the experience even better. We especially loved the jacuzzi area and the large, comfy couch in the living room. The entire place offered great privacy. Would definitely recommend it!

We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)

Reda’s place was absolutely perfect for a week-long stay - I felt so at home. I was visiting family who live just down the road, but needed a space of my own to work and relax between visiting with family; it fit my needs to the “t”. The kitchen was fully stocked with all utensils (even a can opener!), so I was able to cook a great meal after a long day of work. The neighborhood is peaceful and accessible; I loved going for a run over to New Bedford and back. Reda was always around to say “hi”. My family and I will definitely be back! Thank you, Reda!

Both John and Carol were very inviting and friendly—- Carol even came out to bid us farewell when we checked out. The view is just breathtaking…. Could not ask for more… except warmer weather so we could have enjoyed the pool. :). The apartment had everything we needed and more. The fridge was stocked with breakfast snacks and milk and half and half for morning coffee…. Very nice touch. Great restaurant choices nearby as well. Highly recommend the Arms Hotel. Great food, HUGE portions. I would definitely stay again!

The detail inside to the bumble bee theme was great with something new always catching your eye. Was able to check in an hour early and Julia was very transparent with communication.

Kevin was very responsive and accommodating which made our experience a great one. His place was perfect to house our 11 family members. The place was clean and spacious.

What more can I say that hasn't already been said by other guests? The place was perfect for our 35th anniversary get-a-way. Darryl was so on top of things. We had a question and it was answered within 2 minutes. He really is a SUPER HOST.

Located in a lovely neighborhood, this place is a gem! So well appointed, there was nothing we could have needed that wasn’t there! The decor was beautiful and Kelly provided so many extra touches. The kitchen was well equipped, including spices, Keurig Cup Pods, tons of dishes, and utensils. The bedrooms were lovely and very comfortable beds. We can’t wait to come back!!!

We loved our stay! Christina’s condo was comfortable, peaceful and perfectly located. We were walkable to the entire downtown area, museums, the concert venue, walking paths, shopping and restaurants. But the best thing was sitting outside on our private deck overlooking the harbor, with Motif #1 just across the inlet. We almost didn’t want to leave the condo…so gorgeous! And Christina is lovely, making sure we were okay, had everything we needed, so responsive. After the condo coffeemaker stopped working, she kindly offered a gift card to a nearby coffee shop, and before night fell, a new coffeemaker was delivered to the condo! Such a thoughtful host… we will be back!

This was the second time we had stayed at Kristin’s. We loved it so much last year we had to come back! Nothing beats the view from the rooftop deck. Everything you need, to include ample public water access, is just a short walk. We plan on making this a yearly stay. The fact you can bring your pup is an added bonus!

Lovely trip back to Marblehead for my granddaughter’s graduation. This home was comfortable and great care taken to provide more than the basics making it welcoming and like home!

We stayed at Karina's condo for 4 days and loved it! It's close to Fenway Park, subway trains, restaurant's, & local markets. Behind the unit is a beautiful path/park (Southwest Corridor Path) that leads you toward city center. Highly recommend this route if you're exploring the city by foot. We also loved the bathroom shower! We would stay here again & highly recommend!

We had a great stay at this lovely place in East Boston. Everything was spotless and just as pictured. The hosts were also super gracious to let us check in early and store our luggage while we did some more sightseeing our last day.

Chandra is an amazing host; she was very responsive and helpful when we were looking for something to do on our rainy last day. She also supplied umbrellas, which we could not have done without! The place is even cuter in person; it's updated and has a cozy vibe and a nice record player with a good album selection and lots of cool art made by Chandra! My favorite is the Mr. T sculpture! The keypads on the inside and outside building doors are very convenient and simpler to use than having to carry a key. Nice newer shower and comfortable bed. Large kitchen, comfy couch, and just a cute, interestingly decorated apartment. The rooftop patio is so nice...it's got a grill and 360 views. I wish the weather had been nicer so we could have hung out there more. Not really close to many bars or restaurants, but an easy walk to the train station or the bike rentals and a 30-minute (ish) walk to the Fenway Park area. I would stay there again; it felt like home.