Vacation rentals with a kayak in Dennis

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Top-rated kayak rentals in Dennis

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Guest favorite

Cottage in Yarmouth

4.99 out of 5 average rating, 174 reviews

Serenity Views | Waterfront | King | Firepit Kayak

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!!

Nov 20 – 27

G$86,223 GYD per night

Guest favorite

Guest suite in Yarmouth

4.83 out of 5 average rating, 124 reviews

Cape EsCape:2 Rm Private Suite, EZ walk to beaches

location, LOCATION; comfy, contemporary newly renovated (‘21) private bedrm & family rm 0.4mile from neighborhd river-beach, 0.9mi from row of ocean beaches. Separate private entrance. A/C. Queen bed. Outside space with picnic table, chairs, & hammock. Beach chairs provided. W/in 5 min walking distance of bakeries, mini-golf, restaurants, shopping, bike trail, kayaking, & more. Bikes for guests. Child/infant friendly. If you need anything, tell me; please don’t wait & note it in your review.

Mar 2 – 9

G$25,448 GYD per night

Guest favorite

Cottage in Eastham

4.95 out of 5 average rating, 207 reviews

The Breeze Overlooking Minister's Pond

Welcome to an absolutely spotless, pristine, romantic cottage directly on a freshwater pond. Centrally located in beautiful Eastham, the Breeze is within walking distance to the Salt Pond Museum and Visitor Center and hiking trails. Take one of the electric bikes provided and hop on the bike path (the CCRT) which is just down the street. Kayak or canoe on the pond. Featured on WNAV "Romantic Winter Getaways". Award winning recommendations guide provided with each stay. *Sat-Sat in July & Au

Oct 8 – 15

G$55,399 GYD per night

Guest favorite

Home in South Yarmouth

4.93 out of 5 average rating, 209 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

✅ We keep rates low by you bringing your own sheets & towels OR linen service is $125. ✅ Smart TVs in LIving Room & 2 BRs ✅ Waterfront hot tub-Open year round ✅ Fully equipped kitchen w/Carrera marble countertops ✅ Gas Fireplace in LR ✅ High quality down comforters & pillows ✅ Level backyard to lake ✅ Dock for swimming and fishing ✅ 2 kayaks & 2 SUPs ✅ Deck w/sitting & dining area ✅ Patio w/seating & gas fire pit ✅ Sleeps 7 ✅ Pet fee $30/day ✅ Waterfront ✅ W/D Locally managed

Sep 4 – 11

G$172,328 GYD per night

Guest favorite

Cottage in Yarmouth

4.92 out of 5 average rating, 408 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Dec 11 – 18

G$41,138 GYD per night

Guest favorite

Guest suite in Dennis

4.94 out of 5 average rating, 124 reviews

*Bass River Victorian Escape* Central A/C*WiFi

Get away from it all. This beautiful, Victorian semi-detached home is part of a former sea captain’s house. Refurbished to a high standard, it is light and spacious with 2 bedrooms and 1.5 bathrooms, fully equipped kitchen, and a 3-season porch with its own entrance. The open floor plan, central A/C, W/D in basement, WiFi, smart TV, outdoor BBQ, and shelves filled with books and games for all ages will make your family vacation that much better. In Sept and Oct, weeks are 20% discounted!

May 8 – 15

G$55,517 GYD per night

Guest favorite

Home in Yarmouth

5.0 out of 5 average rating, 248 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

Sep 19 – 26

G$120,221 GYD per night

Guest favorite

Home in Dennis

4.95 out of 5 average rating, 151 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Apr 5 – 12

G$52,628 GYD per night

Guest favorite

Apartment in East Orleans

4.94 out of 5 average rating, 259 reviews

Cozy Waterfront Apartment, Private Beach Access

Hello to all of my future guests. I want to wish you all well and safety in these uncertain times. I can assure you that this property is safe, private, spotless and affords you access to a beautiful private beach. I have updated the apartment to include a microwave and two kayaks. We are implicating extra sanitizing and cleaning measures to ensure the apartment is clean and safe for each guest! Please stay safe, optimistic, and let me know of any concerns. Sincerely, Patty

Feb 10 – 17

G$45,655 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 151 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Sep 22 – 29

G$20,562 GYD per night

Guest favorite

Guesthouse in Yarmouth

4.96 out of 5 average rating, 183 reviews

One bedroom guest house on beautiful Cape Cod

Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

Nov 2 – 9

G$36,005 GYD per night

Guest favorite

Home in Harwich

4.98 out of 5 average rating, 129 reviews

* Game Room, Quiet St, NESN, Central AC, 4bd/2ba

Cape Cod - Harwich on Dennis Line - Entire Home; 8 Beds - 4 Bd/2 Ba plus a seasonal outdoor shower - Linens included (a rare find on the Cape), Central A/C, Game Room, Cable, Wifi, NESN, pet-friendly, central to beaches, outlets, golf, antiquing and attractions. Great Central Location! Beaches: Mayflower, Earle, Pleasant Road, Corporation, West Dennis, Crowe's Pasture, Paines Creek, Harwich, Dennis, and Brewster Beaches!

Sep 19 – 26

G$106,109 GYD per night