Holiday rentals with a kayak in Oak Bluffs

Rustic Beach Cottage

The salty air will instantly wash all your cares away. This rustic charming Cape get away is steps away from a quaint quiet picturesque beach. Simply relax in the comfortable surrounds in this fully furnished 1 bedroom Cottage apartment with all of your basic needs including WiFi, Smart TV, A/C, and a deck complete with gas grill and outdoor furniture offering you plenty of living space inside and out. Close to the bike paths, Cape Cod Canal, great restaurants, hiking, ferry and much much more!

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, garden and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

ShoestringBayHouse, waterfront & pool in Cotuit

Memorial Day weekend AVAILABLE, pool is OPEN and kayaks are in the water Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. Our home overlooks the pool, our wading beach & bay. Included: Bikes, Kayaks, and a beach parking pass. Our pet friendly and spacious home with 4 BR/ 4.5 baths is priced for six (6) guests but our home will accommodate up to eight (8) guests at additional cost. (inquire) Bookings made for FALL 2025 may require reservation as non-refundable (10% discount)

Waterfront Cottage / Your Cape Escape

Welcome to our fabulous, waterfront, studio cottage! Come relax and recharge at our beautiful property on Pocasset River, just five miles from the Bourne Bridge. Warm water beaches, bike paths, scrumptious restaurants and fun night spots are abundant and close by:) A lovely, village awaits at your doorstep; walking distance to everything you’d ever need! Your accommodating hosts, Mary Ellen & Dan respect your privacy, but are most delighted to help in anyway to make for your perfect stay!

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Adorable Cape Cod Cottage

Adorable Cape Cod cottage located on 5 acre private residence. Stay at a historically registered property! Large yard with spring fed pond available for swimming, kayaking, fishing or paddle boarding. Cottage recently renovated (2021) with new hardwood floors, paint, and sofa. Great central location close to Hyannis, historic Barnstable village, and Sandy Neck Beach. Close to nightlife and great restaurants, but located in beautiful quiet historical neighborhood.

Swan nest escape

The Swan Nest Escape , nestled on a peninsula in a peaceful private neighborhood, is a charming retreat that offers access to the lake and features a large trail perfect for hiking and exploring nature. The house boasts comfortable accommodations, a fully equipped kitchen, and cozy living spaces designed for your comfort. Whether you’re seeking a romantic escape or a family vacation, our lakeside retreat provides the perfect setting for unforgettable memories.