
Holiday rentals with a kayak in Orleans
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Top-rated rentals with kayak in Orleans
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House rentals with a kayak

The Wellfleet Beach House. Sleeps 6
This is by far the nicest home we've stayed in through airbnb. Everything about the house is beautiful: the furniture, the beds, the artwork, the kitchen, the bathrooms. We could tell that a lot of attention went into the design and decoration of the house. The location was perfect and the house is on a beautiful and well kept plot of land with great outdoor space. Barry was very responsive to our questions and even reached out to see how we were coping with five (!) days of cold and rainy weather. The house made those days delightful!!

* Walk to the beach - Swiss Beach House! *
The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.

Cape Cod Life is Good Rentals
We had a wonderful stay!

Falmouth Summer Escape – Sleeps 6-Dog Friendly!
We have stayed at Brian’s place two years in a row, and it is by far the best airbnb we have ever stayed at. We love the amenities! Also, it is always incredibly clean and has super comfortable beds. Brian is incredibly responsive and accommodating, overall, an amazing host! We highly recommend staying here and plan to come back again!

Private Lake Beach | Spectacular Views & Amenities
This is an absolutely beautiful rental and location. Cleanest, most pristine location we have been to. Appliances and bathrooms are glimmering. Host is immediately responsive and kind. 10 out of 10 in all respects.

Spacious Mid-Cape Home 5 Bedrooms, 9 Beds, 3 Bath
We absolutely loved our stay at Rachel’s! We kept saying “this place has everything”. It was a wonderful home for a multi generation holiday hang. From a 7 month old to great grand parents. The main floor was easily accessible for family member with a disability. We felt right at home with our 7 month old, the home had a pack n play - all set up with fresh sheets, baby bath tub, high chair, bath toys, monitor, etc. The basement was perfect for the teenagers to hangout and have their space. The backyard was peaceful and extended the hang area. Rachel was incredibly friendly and responsive.

25 Menemsha Rd., Popponesset, pond & beach views
Our family had a wonderful stay. The house is in a very special location, with a very short and easy walk to the beach, and right next to a pond. Our boys woke up bright and early each morning to fish in the pond and we could sit on the deck and watch them reel in some nice fish! Hot tub was a nice bonus. The neighborhood was walkable and the beach was really beautiful. Thankful to have found this house and been able to stay for a few days. Host was responsive and easy to work with!

Cozy ranch with private neighborhood beach
The home was lovely. The inside and outside were just as described in the pictures. The home had everything needed in the kitchen for cooking, although we chose to order food for delivery. The neighborhood was very quiet with friendly neighbors. The location was close to groceries and shopping—great locations for the ferries (Woodhole and Island Queen) to Martha's Vineyard. Although my stay was short, the accommodations were perfect! CONS: It was most challenging to navigate the channels on the TV's in the home. I would only recommend having a local channel guide available.
Cottage rentals with a kayak

Spectacular Beach- front home, includes linen
Our stay at Lisa's place was very pleasant. Her home is very nice with a lovely view of the lake and plenty of space for large families (we were only four people but can easily accommodate a few more). The neighborhood does not have a lot of car traffic which is great for walking and jogging around the lake. And it is also relatively close to Falmouth downtown and convenient stores. Lisa was very easy to communicate with and is very courteous and friendly. She really seems to care about her guests' comfortability. It was a pleasure dealing with her. Thank you, Lisa!

Compass Rose Cottage ★ Steps to Flax Pond & Trails
Carol is a great host. We had a small issue with the front door screen locking up and she came over right away and let us in. She is very responsive and responsible. I forgot my medication when I left and she was kind enough to mail it back to me immediately. She has a been a great host and I hope more hosts are like Carol. It rained the whole time we were there so we did not get a chance to check out the lakes around there but I am sure they are great. There is a mall near by with bowling so we did that instead. Thank you Carol for everything. Cheers

Cape Cottage Escape
Amazing and peaceful stay! Can’t recommend this place enough and the hosts! We had the best honeymoon. :)

Cape Escape-The Perfect Getaway
Our stay at Kevin’s cottage was nothing short of amazing! He had everything we needed to make our stay the best, even things you wouldn’t think an Airbnb would have which was sooo helpful! Very clean, the location was in the middle of all the things we wanted to do while at the cape, and just overall a cute little cottage. Loved the outside shower as well!! Kevin was also so helpful with everything and a great host. Couldn’t recommend enough! We’ll be back!

Cottage near bay beach- 1 Bd/1Ba
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!

Beachfront at Days' Cottages! Renovated, Kayaks!
The stay at Larkspur was nothing short of fantastic. The cottage was very clean and well maintained. My wife and I had the privilege of having our honeymoon here and I would recommend it to everyone. We can't wait to come back with our future family!

The Lemon Drop Cottage- Swan Pond River Views!
The Lemon Drop was perfect! Just like the pictures with a clean beachy inside and amazing outdoor space. We had a wonderful time with all the amenities easily available. Great communication throughout our stay

Modern Cottage on 6 Acres -Walk to Beach and 6A!
This place was absolutely amazing! Nice and private but conveniently located. The house was very comfortable and had all the amenities you need. Close to the beach and all the best spots in Brewster. My son’s favorite part was Basil the dog, who would come greet us as we hiked the expansive property. Would highly recommend and would stay here again in the future!
Quick stats about holiday rentals with a kayak in Orleans
Total rentals
20 properties
Nightly prices starting at
₹14,646 before taxes and fees
Total number of reviews
730 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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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