
Holiday rentals with outdoor seating in Dennis
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Top-rated Holiday Houses with Outdoor Seating in Dennis
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Holiday House Rentals with Outdoor Seating

Romantic little Cape Cod Cottage on Rail Trail
Our stay at this charming, one-bedroom cottage was everything we hoped for and more. From the moment we arrived, we were enchanted by its storybook charm—complete with a white picket fence and blooming flowers. Inside, the exposed beams and cozy décor gave it the perfect blend of rustic and coastal charm. We started every morning on the back deck, sipping coffee and listening to the birds—it truly felt like a hidden sanctuary. The house itself was spotlessly clean, well-maintained, and thoughtfully stocked. The water pressure in the shower was amazing (not always easy to find but greatly appreciated), and every detail felt considered. There was nothing we needed that we couldn’t find within its white cabinets. It was quaint and quiet, but still conveniently located to beaches, shops, and restaurants. A perfect blend of nature, comfort, and Cape Cod magic. We'd come back in a heartbeat and hopefully have slightly better weather!!

SUMMERS OFF CAPE HOUSE
We really enjoyed the comforts of Antonio and Meghan's home as well as the location and walkability to the ocean. Nice, quiet neighborhood. The process and communication with them was easy and flowed. 5 stars all around and would highly recommend!!

*NEW* Spacious Family Cape House 10min to Beach!
We had a lovely stay! The house was very clean and looked exactly like the photos on the listing. It had everything we could possibly need during our winter getaway. The host sent clear and helpful instructions and we had no trouble getting into the house or finding the things we needed.

Sunny, bright 4b/3ba Cape Cod house, near it all!
This was our second stay at Erica and Chris’s and we had a blast! It’s exactly as advertised, extremely clean, conveniently located, and the hosts are so friendly, helpful, and responsive! Highly recommend!

Adorable Cottage - Premier Location in West Dennis
Excellent stay. Chuck was great! We traveled with a child and it was very accommodating. Very close to the beach.

Modern Cape Home near Beaches,Firepit, EV Friendly
Nina's cottage is one of the nicest Airbnbs that we have rented. It is beautifully furnished, with modern decor, the kitchen is very well equipped for cooking, all items are organized and identified. The outdoor space is very spacious and pleasant. The location provides easy access to the south and north parts of the island. Within a short drive, there are excellent restaurants ranging from casual lobster shacks to an upscale sushi spot. Nina is a wonderful host; we found her to be responsive, friendly, and informative. We will definitely rent this house again.

Family Retreat in the Heart of Cape Cod!
Comfortable and well-equipped house in great central location for exploring the Cape. Keith is so responsive and reliable. Would stay again.

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK
We had a very relaxing stay at this property. Very comfortable bed and home. Staying on the pond was very calming. Though the weather did not allow us to use the kayaks, we could see that it would have been fun. Host was very responsive and helpful. Fabulous stay! Highly recommend this great place!
Apartment rentals with outdoor seating

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Such a lovely place! Peaceful, super clean, and overall excellence! Best Airbnb experience I've had so far!

Brand new! Whole apartment, huge tub, full kitchen
If I could give 100 stars I would!! Out of all the airbnbs I have stayed at Jennifer’s listing has outdone them all!! First of all, Jennifer was the most amazing host and treated us like family! Secondly, the house was spotless, not a speck could be found (and I am usually picky about cleanliness) — it was absolutely exceptional!!! I will definitely be coming back multiple times. Thank you Jennifer for hosting us!

The Knoll
Peg’s home was perfect for our stay in Chatham. It was quiet and peaceful but close enough to Main Street and everywhere we would want to go during our visit.

Centerville Studio with Town Beach Pass
Great internet. Super clean. Would definitely stay again. Five stars.

Sunny Studio Apartment on Martha's Vineyard
We had such a great stay! The hosts were super accommodating and really attentive to anything we needed. The place was spotless, cozy, and fully stocked with all the essentials (and then some). They went out of their way to make us feel at home, and it honestly made the whole experience so relaxing and enjoyable. We loved everything about our stay and are already looking forward to making this an annual tradition! Tracy Thomas and Drenary Gwynn Baltimore Maryland

Stylish retreat | walk to town | fire pit
The apartment is just perfect for a week on the Vineyard, and Jennifer has thought of all the details. So easy to use and find everything. And it is a lovely space.

Cozy Waterfront Apartment, Private Beach Access
My fiancé, dog Bandit, and I stayed here for a few days and it was comfortable & had everything we needed. The private beach was a 10/10. Perfect place to watch the sunrise and there are gray seals constantly swimming by near the shore, so cool!! Make sure you take a look at the ideas and recommendations that Patty left in the blue ring binder. I recommend the Rock Harbor Grill for dinner & Ice Cream Cafe for dessert. Close by to the awesome rail trail for dog walks and only a 50ish minute drive to the tip of the Cape Cod National Seashore. I will say BEWARE of ticks if you’re walking your dog. They are plentiful in Cape Cod, believe it or not. Finally, Patty was a wonderful host. We would definitely choose this Airbnb when visiting Cape Cod again.

A quiet, private, unique spot in a great location!
Lisa’s place is perfect and just what we needed. Very clean and got everything you need, close to so many beautiful spots and lots of dining options in the area. I’ll miss Lisa’s beautiful property and serene nature backyard. Thank you
Condo rentals with outdoor seating

Serene, Cozy, Waterfront, 3 Mi to Downtown!
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Clear Pond Pet Friendly Inn
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
Anna’s place was exactly what we needed to have a peaceful and relaxing Memorial Day weekend stay. We knew the weather might be on the cooler side, so purposefully wanted to stay where there was the possibility of using the indoor pool – the sponsored guest passes were a huge benefit here, and Oceans Edge staff even went above and beyond, adding an extra day to our pool access since we were picking them up so late in the day. The condo was clean and filled with all the essentials, in a very quiet area of the property. Would definitely stay again!

Steps to Private Beach in Chatham
Great location for a quiet, peaceful Cape Cod family getaway. Perfect space for group of 4, located on quiet corner of Chatham/cape cod. Very walkable to downtown and lighthouse beach (best beach in cape cod). Julia is a wonderful host, extremely responsive and her local recommendations for visitors were outstanding, especially for first time visitors to CC. Would recommend.

Hidden Hideaway
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.

Bright & Breezy Bayside Condo
Joanne’s place was spacious and comfortable. There was plenty of closet and drawer space and it would work well for an extended stay. It’s quite near the beaches and harbor in Dennis/Quivet Neck, and there is a good restaurant (Marshside) with a scenic view that is a short walk away. Easy to find, although if you check in at night a flashlight will be very helpful. ;-) The kitchen was small but usable, and the refrigerator was modern and had plenty of room.

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
We really enjoyed our stay. Great condition, really clean, easy parking, and great location right at the Ocean Edge resort. Rob was an excellent host, super communicative and responsive. Would stay again!

6 Min to Beach - Pool - Private Balcony - Central
My boyfriend and I stayed in this beautiful and quaint condo for a wedding weekend in Dennis and it couldn’t have been a more perfect place with a more perfect location!We both felt safe and comfortable immediately upon arrival and loved spending time outside on the porch and enjoying walking around the area! We would both recommend this stay to anyone!
Quick stats about holiday rentals with outdoor seating in Dennis
Total rentals
770 properties
Total number of reviews
33K reviews
Family-friendly rentals
630 properties are a good fit for families
Pet-friendly rentals
210 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
350 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- Onset Beach
- Inman Road Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Cahoon Hollow Beach
- Kalmus Park Beach
- White Horse Beach
- Peggotty Beach
- Cape Cod National Seashore
- Forest Beach
- Linnell Landing Beach
- Ridgevale Beach