logo ×

Chatham is a charming community, on Cape Cod it is located halfway between the Cape Cod Bridges and Provincetown. This coastal popular town offers many exciting activities and attractions that can make your Massachusetts vacation memorable. Chatham is situated on the “elbow” of Cape Cod, and is surrounded on three sides by water. Chatham offers uncompromising beauty. Visitors are drawn to the pristine beaches, the historic lighthouse, quaint downtown area, and of course the ocean views. Just a short distance from our Chatham vacation rentals, you’ll find the town of Chatham, a lovely combination of the present and the past. Stroll along streets dotted with sea captains’ homes and historic museums. You’ll find landmarks of days long past signifying the town’s history as a once quiet farming and fishing community. Enjoy wonderful restaurants, shopping and the best homemade candy and ice cream around. View our assortment of Chatham MA vacation rentals below and #BookNEVRDirect!

From Mid June to until Labor Day–7 Night Friday Arrival is Required.
If you need help planning a shorter off-season stay, please contact our reservation team.

Book Our Chatham MA Vacation Rentals Below!

Ocean View
Private Beach Access
Walk to beach (.5 or less)
Waterfront (Lake/Pond/River)
Walk to town (.5 or less)
Bike Trail (.5 or less)

Central Air Conditioning
Slimline A/C - ductless
A/C Units
Heat (for off season)
Linens Included
Fully Fenced Yard

Private Pool
Community Pool
Private Hot Tub

Dog Friendly

On Special

Unable to find any listings.

Beds | Baths | Half Bath | Guests
Central AC

Showing of properties

Use That Kitchen

Our Chatham MA vacation rentals are designed to have every inch of space lived in and used, and that includes the fully equipped kitchen! Why not take advantage of the great deals you can get at the Chatham Village Market, located at 20 Queen Anne Rd, and pick up some ingredients to create a home cooked meal? Our kitchens are stocked with all the equipment needed, pots, pans, dishes, and silverware, but we left the food shopping to you. Our kitchens take the chores out of meal preparation, but if you just don’t feel like cooking while on vacation, the baked goods sold at the Village Market are fresh and sweet and make a great midnight snack; since you’re going to need some wine for your vacation, grab a bottle or two while you’re there!

Taste of the Town

Whether you are planning on eating every meal in Chatham or just want to sample a bit of what our village has to offer, your choices are extensive. Restaurant owners in this town truly care about offering quality meals. Breakfasts at Hangar B Eatery at 240 George Ryder Rd are made even more special by its location inside the Chatham Municipal Airport. Watch the planes take off and land as you enjoy your potato buttermilk pancakes! Sandi’s Diner at 639 Main St offers delicious diner meals that taste as if you could be lunching on a dish your mom created—nothing fancy, just good old-fashioned comfort food that sticks to your ribs. For a unique and savory dining experience, you have to try the Impudent Oyster at 15 Chatham Bars Ave, located inside a former church! Serving lunch, dinner, and beer and wine, the seafood is always fresh and the oysters are out of this world!

It’s the Natural Beauty That Makes Chatham so Special

To be perfectly honest, all of Cape Cod has that rugged natural beauty that makes you feel as if you could be a professional photographer. Every picture you take looks amazing! Chatham, however, is home to the Monomoy National Wildlife Refuge, a federal wildlife preserve dedicated to the preservation and protection of our native birds and other wildlife. They have created “safe zones” so they can migrate back and forth without danger. At various times throughout the year, some areas may be closed, so be sure to check their website (https://www.fws.gov/refuge/Monomoy/) before you visit, and whatever you do, don’t forget your camera!

Things to Do and See in Chatham

One of the best parts of staying in our Chatham MA vacation rentals is the many close-by beaches. You’ll find 10 lovely beaches through the village, where you can spend a day or two exploring the sandy shores or just lounging beneath an umbrella enjoying the ocean breezes and views. The Chatham Bike Trail is a great way to get around town.

Sport fishing is one of the area’s favorite activities, and there are plenty of opportunities to try your hand. You can fish from shore at several landings, and there are fishing tours and charters that will take you out on the ocean waves for some exciting deep-sea fishing. Don’t forget to visit the Chatham fish pier and watch all the fishermen bringing their catch of the day in.

One landmark that should not be missed is the Chatham Lighthouse. Offering tours in the summer season, you will be able to experience this delight first hand. From the top of the lighthouse, you will gaze upon gorgeous views of the surrounding area and the ocean. Other great activities include golfing, a lively theater community, concerts, and more.

Where to Stay in Chatham: Our Chatham MA Vacation Rentals!

When it’s time to make your vacation plans, choose from one of our Chatham vacation rentals. These vacation accommodations will give you far more amenities than a regular hotel stay. Our Chatham MA rentals include everything from charming cottages to larger, expansive homes.

At New England Vacation Rentals, we have numerous choices of Chatham MA vacation rentals, so you can find the best accommodations whether you are coming for a romantic getaway or a family vacation. Let us help you find the best Chatham Cape Cod rental for you!

To book Cape Cod rentals in specific areas, click the links below:

And if you’re interested in learning more about the area, visit WikiTravel to find out all you need to know! (https://en.wikivoyage.org/wiki/Chatham_(Massachusetts))

FAQs About Chatham Vacation Rentals

Q: Can we get married on the beaches of Chatham?

A: Beach weddings are popular on Cape Cod, so go ahead and make your dreams come true during your Chatham getaway, just be sure to file the proper forms requesting permission found online at the Town of Chatham Parks and Recreation website.

Q: Our wedding is going to be a destination wedding in Chatham and we would like for our guests to all stay in the same home. Does New England Vacation Rentals offer homes for large parties to rent?

A: We offer a large variety of homes of all sizes in Chatham with our largest escape providing room for up to 20 guests to live together in comfort and harmony.

Q: We like to taste foods that represent the areas we are visiting, what do you recommend we try while on Cape Cod?

A: Lobster in butter sauce is our top choice but if that is a little expensive for your tastes, fried fish and fried clams are a great second choice that won’t break the bank. Macs Chatham Fish & Lobster, located at 1291 Main Street, is a great place to try both those dishes.

Q: I’m looking for an unusual gift to buy for the person who is checking my mail while I am on vacation, where can I go in Chatham?

A: One of the more unusual shops in Chatham is called Ducks in the Window, selling exactly what they advertise, rubber duckies! Located at 507 Main Street in Chatham, their ducks are famous all over the world, coming in all shapes and sizes and can even be personalized for added enjoyment.