Guest house holiday rentals in Dennis

We had a great stay with Peggy! She is wonderfully kind and we had everything we needed to relax and adventure on the island. Such an amazing location and cute, cozy space, would highly recommend!

Joe’s place was absolutely perfect! It had everything we needed and made our Cape stay truly memorable. The location is ideal—close to several beaches, great restaurants and local ice cream spots. It’s also a great base if you want to explore other Cape towns nearby. Joe was super communicative and helpful throughout our stay. We’d absolutely stay here again!

This is my husband and I’s second time staying at Dawn’s cottage and we still absolutely adore it! Even more so than the first time! Super clean and has absolutely everything you need. Not only is it stylish, but it is home-y too! Dawn and her husband are responsive and so nice - we are very thankful they share their place with us! Until next time, cottage and MV! We’ll be back again!

Valerie and Kevin were fantastic hosts - incredibly kind and great communicators. Their guest house was the perfect spot to explore the cape from. Peaceful and a short walk into the cute downtown of osterville. Would highly recommend!

the place was comfortable, spacious, very clean. The kitchen was well stocked. very good shower. Of note, if you are a very light sleeper like me, there is an apartment upstairs. The person living above us was extremely quiet but I was woken up by the sound of the toilet flushing upstairs on some early mornings. Only because I am a very light sleeper. The refrigerator is also quite loud (older model) and since this is an open space design, some of my family members noticed and found it annoying. All in all we enjoyed our stay and would rent this place again!

We really enjoyed our stay at this cottage. It was clean, comfortable, and close to town and the beach. Michael was an excellent host!

This cottage is perfect for privacy, coziness & location in Wellfleet. Kitchen well accessorized for everything you needed. It rained a lot during our stay, so the size and furnishings mattered for staying in and this cottage hit the mark. I have stayed in several locations in Wellfleet & Ptown and highly recommend here for the walkability to Main St, convenience to other Cape Cod towns, & central for many restaurants and beaches. Unfortunately we didn’t get to use the yard much due to weather and our other activities, but it seemed large and private. Just a lovely home for a week on the Cape!

We had wonderful days at Big Chill. The cottage and main house is located very privately in a wooded area and surrounded by a beautiful garden, creating a magical space in nature. The cottage is very beautiful, bright, clean and has most things you need.We liked especially the upper floor where all beds were in one spacious room The cottage is entirely designed and built with care and character, craftsmanship, an artistic eye, and much heart by the hosts Kati and Mark. And they are ,as well ,very caring about their guests. They enjoy having guests and helping them, which creates a unique place where we felt very well and being in the right place.Thank you for creating such a nice place and sharing it with all your guests.

Dan is such a warm, hospitable host! He welcomed us upon our arrival and helped up get settled and introduced the rich history of the cottage. We were a group of 5 high school seniors, and this place was perfect for our needs to relax on the beach! Dan provides a wagon from the shed and we borrowed his beach chairs and simply rolled them out onto the beach with a 5 minute walk. It was relatively quiet, and I loved the homey, cozy vibe, and I got two amazing nights of sleep during our stay. For the price of this AirBnB, you cannot beat the location! Walk back into the backyard, and you’ll arrive in downtown! For both mornings, our crew went to Cape Roots Cafe & Market for a lovely breakfast, and there was just enough to explore for our 2-night stay! I would highly recommend Dan’s establishment for anyone looking for a relaxing, laid-back stay at Cape Cod.

Had a delightful second stay at Carolyn and John's B&B...clean, beautiful, peaceful. They were responsive quickly, and made us feel at home. John met us as we arrived and we had a pleasant chat with him. We have stayed here before, and will stay again! Thank you!

Beautiful cottage! Thank you, Mary Ellen and Dan, for your attention to detail and the many thoughtful touches! Everything was at our fingertips…from robes and slippers to clean, crisp linens! The cottage is quaint, clean and comfortable! This little oasis is quietly tucked away, yet allows quick and easy access to all that the Upper Cape has to offer! Thanks again! Kevin and Nancy

We had a wonderful time in Yarmouth and this was the perfect place to stay. Thank you!

This property is great, so close to the downtown area and the surrounding neighborhoods, you can walk to everything which made going out to dinner and shopping very easy.

We really enjoyed Rebekah and Tim's place. Right when we arrived, Rebekah made us feel very welcome and the place was just as the pictures showed: beautiful, peaceful and cosy. After a month working in the big city New York this place was perfect to wind down and relax. Rebekah has a list of all things to do and lots of great recommendations we tried and enjoyed. We already miss this place and would love to return on day!

Allison is a dream host. We stayed at the cottage for our engagement and proposal trip and couldn’t have picked a more perfect place for it. Allison created a magical Cape Cod experience full of beautiful details including fresh flowers, relaxing hammock, chill breakfast deck, whimsical treehouse, soft bedding and wonderful kitchen with views of nature. Everything is designed with fine taste and genuine care. Line of sights flow elegantly and framed beautiful views throughout the space. She left us handwritten notes and generously prepared the space for our engagement photoshoot. We had such a peaceful and romantic time at the cottage that it felt like a sweet home away from home. We left with lots of happy memories and inspirations. Thank you Allison. We truly loved the space and would come back again in a heartbeat!

We thoroughly enjoyed our stay! The cabin was very clean and in a quiet neighborhood within walking distance to a sandy beach and excellent seafood restaurant.

Our stay in Martha’s Vineyard was perfect. The Clamshell was beautifully decorated and was extremely clean - even better than the pictures. The location is outstanding and made it easy to come and go. We felt right at home during our visit. Nancy’s hospitality is unmatched.

Genainna and her husband were wonderful hosts. Our schedule was turned upside down twice, and they did not hesitate to accommodate us. They were focused on ensuring we would be able to come and enjoy our stay, and we greatly appreciated it! They made it seem like it was their pleasure to reschedule us. Genainna was always very responsive, providing wonderful recommendations and helpful tips. The garage unit is very clean and well stocked. The stairs to the loft were a bit steep and unnerving, but our 18 year old daughter was ok with them.

We had a lovely stay at this Airbnb in Brewster. The place was exceptionally clean and well-maintained, which made us feel comfortable right away. The location is fantastic, quiet and peaceful, yet just minutes from everything we wanted to explore in Brewster, including beaches, restaurants, and the bike trail. It was the perfect home base for our Cape Cod getaway. Highly recommend!

Christin was a gracious host and very responsive to our needs. The only thing I would have any complaints about is that it was a very hot week when we stayed and since there was only one AC upstairs where the two bedrooms are it was quite hot in the bedroom that didn’t have the AC. Other than that, the place was very charming and we very much enjoyed our stay

Lovely home, well-maintained and quiet. A beautiful place to rest as well as easy access to bike trails and towns. We used the outside shower the whole time and it was so refreshing. Had an incredible dinner at Lambert’s Cove in the garden.

This Airbnb was perfect for our stay! The apartment was spotless, had everything we needed, and the location was ideal. We appreciated the thoughtful touches and the host’s helpful communication. Would absolutely stay here again!”

We had a great stay at Cristian and Yuri Paola's place. It was just like the pictures and very quiet and relaxing but near to everything Cape Cod has to offer. Thanks so much for all your help during our stay!!

Mary Lou and Bill were exceptional hosts and their property was absolutely stunning. We stayed in their carriage house with our 3 children and it was a perfect fit. Our kids loved the shuffleboard table and there was plenty of space for them to lounge after a day at the beach or exploring the Cape. They were super generous allowing us to use their coolers, towels, beach chairs, etc. If we had any questions Mary Lou was always very quick to respond and make us feel at home. I’m not sure the pictures do this property justice; again just absolutely stunning and the perfect place for our summer vacation in 2024. Would love to come back and couldn’t recommend it any higher!