Cottage vacation rentals in Chatham

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Top-rated cottage rentals in Chatham

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Yarmouth

4.99 out of 5 average rating, 175 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!!

Oct 20 – 27

G$95,755 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 103 reviews

Steps to the Beach Kid Friendly

Sip your coffee on the patio or at the water with the sandpipers , spend some family time at the swings, making sandcastles or swimming in the warmer waters of Nantucket sound. It's all just footsteps from your door! Nip back to the cottage to cool off before heading out to enjoy the local attractions. You’ll also be just 3 miles from the bike trail! Return for a blissful end to your day watching a beautiful Cape Cod beach sunset and enjoying the starry sky. *Positive reviews required please

Jul 13 – 20

G$80,084 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 217 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

Nov 9 – 16

G$34,882 GYD per night

Guest favorite

Cottage in Chatham

4.96 out of 5 average rating, 217 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property.

Oct 16 – 23

G$48,213 GYD per night

Guest favorite

Cottage in Orleans

4.93 out of 5 average rating, 128 reviews

Cape Cod Cottage with view of Orleans Town Cove

The cottage is very clean, cute and comfortable and has every thing you might need. Situated in a quiet, friendly little neighborhood, right next to the famous Cottage Street Bakery, yet you would never know you are so close to town! It is centrally located within walking distance to restaurants, shops and bike path, with the Ice Cream Cafe right down the street on the corner. 3 miles to all beaches. Access to the Cove including kayak rental is just down the street. Perfect location!

Oct 14 – 21

G$60,154 GYD per night

Guest favorite

Cottage in Yarmouth

4.92 out of 5 average rating, 411 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

Nov 11 – 18

G$41,045 GYD per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a sought after cape style cottage community. It offers a Private Association Beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal 5 min away. Close to restaurants, hiking trails, and Mass Maritime. Cape Cod Bridge 5 min away. 20% off wk!

Apr 17 – 24

G$28,291 GYD per night

Guest favorite

Cottage in Harwich

4.9 out of 5 average rating, 134 reviews

"Coaster" Village Location!

Sweet Cottage just a 1/2 mile to Bank Street Beach and only a block from Main Street. The property has lovely gardens and landscaping making it a wonderful retreat setting. Summer months July, August to Sept 10th are 1 week rentals Saturday to Saturday unless a few days are available in between or if there is availability as season approaches. Off season, 2 to 3 night stay minimum, I provide linens, coffee and towels for short term rentals. Easy walk to the village and beaches!

Sep 25 – Oct 2

G$47,934 GYD per night

Guest favorite

Cottage in Chatham

4.94 out of 5 average rating, 145 reviews

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

Sep 23 – 30

G$78,034 GYD per night

Superhost

Cottage in Dennis

4.88 out of 5 average rating, 353 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Our cottage (Graham Cracker House) sits steps from crystal clear White Pond. The cottage offers private access to the pond for swimming, fishing and boating. The large outdoor space is great for dining and relaxing by the pond. It is 1.5 miles to the Cape Cod rail trail (bike trail), close to many dining options and 3 miles to some of the best beaches Cape Cod has to offer. There is another cottage on the property for rent that sleep 4 guests. No sharks here!

Nov 18 – 25

G$42,192 GYD per night

Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 344 reviews

Barn Cottage on Minister Pond

Newly renovated cozy heated Barn Cottage (not attached to house- privacy!) on Minister Pond with dock access to canoe/ new queen size bed/equipped kitchen/large deck overlooking pond/gas grill/private yard/2 minutes to ocean or bay beaches and bike trail in National Seashore/ many local attractions, and restaurants! Please note the new 12.45% short term rental tax is now in effect and will be added to your base. Thank you

Oct 30 – Nov 6

G$29,909 GYD per night

Guest favorite

Cottage in Eastham

4.91 out of 5 average rating, 189 reviews

Classic Cape Cod Cottage

15 min walk to the best bayside beach. Very peaceful setting. Four night minimum stay from April 15 to June 15. June 15 to Sept 10 there's a 7 night minimum stay, from Saturday to Saturday. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore.

Apr 22 – 29

G$33,333 GYD per night