Chatham Vacation Rentals

(1 rental)
Our Great Gatsby

9 BR | 3 BA | Sleeps 19 | Quick View

About this property

This family estate was built in the 1930's by Mr. & Mrs. John Peale Bishop, a famous writer and poet and best friends of the infamous F. Scott and Zelda Fitzgerald, and is nestled on 1.3 acres overlooking the beautiful salt marshes and the ocean! It is ideal for family reunions, vacations, girl getaways, ...

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Chatham House

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Chatham Vacation Rentals

Soak up the fun and sun in your Chatham vacation rental

Chatham offers vacation goers a classic Cape Cod experience. Its population swells during the summer with people locking up vacation rentals and hotel rooms months in advance. The town sits on the elbow of Cape Cod and its villages (Chatham Port, North Chatham, West Chatham, South Chatham and Chatham proper) sit nestled between the Atlantic Ocean, Pleasant Bay, and Nantucket Sound. This makes the town a stellar spot for beaches and outdoor activity. Add in great restaurants on Main Street and the town's historic charm and culture, and it's easy to understand why vacation rental houses in Chatham are so popular. has a wide selection of rental options in each Chatham village for any size budget and guests.

Chatham, MA travel advice

Packed with tradition, attractions, and events, Chatham offers a sought-after Cape experience. With many residents and long-time guests, we recommend getting your search for a vacation rental in Chatham sooner than later. Particularly if you're considering a visit in early July and around the Fourth of July. Some of the patriotic festivities around the 4th have been around since World War II. Many proponents for Chatham claim this is the best place in the country to celebrate the birth of our great nation. So our advice to booking a rental here is: go, now!

Top attractions

Chatham Lighthouse sits basically at the pointy part of the elbow of Cape Cod. It's a great sight to see around dusk and after sunset because, you guessed it, the lighthouse works. It's a marvel to see it do its thing. Plus, the lighthouse abuts a beautiful, pristine beach -- Keegan Lighthouse Beach, which is regularly recognized by locals and tourists alike as a favorite. There's limited parking near the lighthouse so get there early. It's a great if small beach to watch the sunrise and, with the Nauset Beach peninsula just off the coast, see the natural beauty of the Cape's unique coastline.

The arts and culture have a good summer home here in Chatham, too. Primary attractions include Chatham Orpheum Theater which is over a century old and doesn't even require you enter it to find it impressive. The theater's exterior is lit up at night and its shining light exterior goes quite well with the films and events you may find inside its walls.

If a part of your beach vacation includes scouring the shores during low tide, then Monomoy National Wildlife Refuge is a must. You can walk the beach all the way to a marsh and find sea shells, sand dollars, sea life and more in the tide pools. It's open year round, which is nice too

Beachcomber Boat Tours on Crowell Road. It's a unique spot for a boat tour with Pleasant Bay and a string of islands just off the coast of North Chatham. You're basically guaranteed to see seals and other fun sights. It's a one of a kind, classic Cape Cod experience.

Family-friendly activities

This is a coastal town and many of its charms are therefore related to the ocean and the shoreline. So it should come as no surprise that Chatham Fish Pier is high on our list of recommended activities for families. A picturesque pier on the Cape? Yes please...

Families who love history should make a pass by Chatham Windmill which is nestled next to Mill Pond and isn't too far from the main drag of restaurants and attracts on Main Street. It's a quick trip but a wind mill built in the 18th century will definitely catch your attention. Also near Main Street is the Chatham Railroad Museum (but it's north Main Street route 28). It's really fun and unique experience for the kids and adults to walk through a super old rail car. Highly recommended.

Music-loving families will love the Chatham Town Band during the summer weeks. It too is right on Main Street so it's super easy to access. Bring a picnic and your dancing shoes or dance shoeless. Its "Band Time in Chatham" is a Fourth-of-July tradition dating back to 1945!! Even if you're not in Chatham for the 4th, Friday nights for the family are better here with some live, outdoor music.

Recommended food and restaurants

Chatham has a legit food scene. It's like no other on the Cape and people come from near and far to its top spots. If you book a vacation rental in Chatham, then you can take your time and slowly work your way through your options. But if your vacation rental is in another part of the Cape or in a near-by town, then you need a plan. But here's the deal:

In some ways, the food options here are a "tale of two cities". There are many great spots clustered around Main Street in Chatham's town center, and then a select few "must visit" spots outside of that cluster.

Let's start with the latter first...Along Shore Road that connects to North Chatham, vacation goers and foodies alike flock to Chatham Pier Fish Market. It's a popular spot for, you guessed it, fish and seafood (fried and not). There can be a line but it moves fast and is worth the wait. While technically still on Main Street (but west of the circle it's called Route 28), Mac's Chatham Fish & Lobster restaurant is a can't miss dine-in experience. Yes, this is associated with Mac's Seafood which has expanded its footprint on the Cape.

Ok, on to the Main Street scene. The thing is, there's simply too many great (and busy) restaurant options in Chatham. To call out a few: Imprudent Oyster is an upscale experience on Chatham Bars Ave. It's a good date spot and bar scene in a converted church. For a cheerful and lively time, try the Chatham Squire -- but know that many a tourists and vacationer will have the same idea.

A fun aspect of staying in Chatham is that these Main Street area restaurants are diverse. There are definitely options for New England classics like great fried seafood, lobster rolls, and ice cream. But there's also Japanese, sushi, Mediterranean and even a wine bar.

Bottom line: if you're a foodie seeking a classic Cape vacation, book a vacation house in Chatham and you won't be disappointed.

Chatham vacation rentals on Cape Cod Vacation Rentals

Sure, finding and booking one of our vacation homes in Chatham on saves you time and money. But more importantly, our selection of rentals will help you find the perfect option for an amazing summer vacation on the Cape. We have a huge range of options that can accommodate any size party. Find yours today!