Discover a selection of 3,000 vacation rentals in Chatham, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $134 per night, and houses and cottages are popular options for a stay in Chatham. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chatham
Destination guide

Find beachfront fun with a Chatham house rental

Enjoying the most coastline of any town in the area, Chatham features Cape Cod house rentals with plenty of space and very short walks to the water. Gorgeous sunsets make this lovely town glow by evening. Visit the picturesque Chatham Lighthouse or some of the many historic homes and buildings to learn the area’s history. If you visit in July, don’t miss the Cape Cod Hydrangea Festival, which features tours of meticulously maintained private backyard gardens and benefits local nonprofits.

Things to do

Tourist attractions near Chatham vacation rentals

Chatham offers many points of interest for history lovers and is a great place to explore Cape Cod’s maritime past. Originally a fishing village, the town still boasts its famous lighthouse, with many of the buildings dating back to the 18th century. Visit Chatham’s popular railroad museum, which dates back to 1887 and houses hundreds of exhibits, including both models and full-size engines that the whole family will enjoy. Experience the area’s colonial past at Caleb Nickerson Homestead, or see how life in the area used to be at Chatham’s Old Grist Mill, built in 1797.


Things to do near Chatham vacation homes

No visit to Chatham is complete without a day at one of the area’s pristine, white sandy beaches. You may even catch a glimpse of the local seals at the famous Chatham Lighthouse Beach, or handsome Harding Beach. The area is well-suited to sea lovers, with many exciting ways to enjoy the waves. Chatham vacation rentals mean you're in a prime position to get involved in the local sport-fishing scene, hire a boat for the day, or take a windsurfing lesson. Alternatively, sign up for a seal tour and get a close-up view of these fascinating creatures.


Local weather for your trip to Chatham vacation homes

You can't beat Chatham for a warm, sunny beach holiday complemented by Cape Cod’s cool, Atlantic breeze. The town is at its most lively in the summer months when the weather is reliably warm, with comfortable average highs of around 70 F between June and September. The weather makes the area perfect for outdoor activities such as hiking, biking, or golfing, with wonderful views of the Atlantic Ocean from the Seaside Links. Many Chatham vacation rentals are located within walking distance of the area’s white, sandy beaches.

Natural features

Keep an eye out for nature in charming, coastal Chatham

With a Chatham vacation rental, you'll be a hop, skip, and a jump from some of the northeast's most compelling natural splendor. Thanks to its position on the Atlantic, the area has plenty of broad, sandy beaches and rocky coastline, most of which offers scenic views of the calm Nantucket Sound. If you enjoy birdwatching then don't forget to pack your binoculars. A complex ecosystem of marshland and sandy dunes, the 7,600-acre Monomoy National Wildlife Refuge is a popular destination where you can see intertidal life and numerous species of migratory birds.

How to get there

How to get to and around Chatham

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 16.8 mi (27 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Nantucket, MA (ACK-Nantucket Memorial), which is 29.9 mi (48.1 km) away.

Family friendly

Family attractions near Chatham vacation rentals

Chatham has plenty of family-friendly attractions for kids of all ages. Vacation homes are close to places like the Cape Cod National Seashore, a shoreline with miles of dunes, sandy beaches, salt marshes, and hiking trails, and the Chatham Lighthouse, a historic lighthouse with a keeper’s cottage and spectacular views. You may also like Monomoy National Wildlife Refuge, a protected habitat for migratory birds and salt and freshwater marshes.

Good for couples

Romantic vacation homes in Chatham

Couples looking for romance can enjoy an array of attractions in Chatham. Vacation rentals can be found near places like Atwood Museum, a restored historic home with galleries exploring the history and culture in the region, and Kate Gould Park, a vibrant park with recreation areas and festivals. You'll also like Linnell Landing Beach, a bayside beach with scenic sunsets and calm waters for swimming and kayaking.

What are the top vacation rentals in or near Chatham?

The heart wants what the heart wants, and right now it's craving a vacation. Now's the time to pack your suitcase and head to one of these top vacation rentals in or near Chatham:

  • "Luxurious Estate Includes - Tennis Court" is a guest favorite. Around 25 miles from Chatham, it has 6 bedrooms and plenty of handy amenities, including a separate dining area and nearby ecotour services.
  • Alternatively, get comfortable at "Oceanfront Contemporary Home - Breathtaking Views". Located around 25 miles from the heart of Chatham, it has 3 bedrooms and features an ice maker and a kitchen island.

For even more great options, use the search bar at the top of the page to find the perfect Chatham vacation rental for you.

What are the best tiny house vacation rentals in or near Chatham?

For an unforgettable experience, book a tiny house rental in Chatham. We'll warn you though — after you've stayed in a tiny house, the urge to move into one of these pocket-sized digs will be hard to resist!

  • Take time off and experience a simpler way of life at "Marion Village's Very Best Cottage - Tiny Home Living Close To The Town Beach". Located in Marion Center, a garden and a dryer are just a couple of the amenities included here.
  • "Stay In A Tiny House 0. 4mi To Beach Village Restaurants Pet Friendly 2 Bikes" offers convenient extras like heating and cookware, dishware and utensils. Located in Dennis Port, you'll be able to live large in this small but nicely designed home.

Can I find log cabins to rent in or near Chatham?

You can. From rustic hideaways to high-end escapes, we've got a wide range of log cabins to rent in or near Chatham. If you're into adventure, look no further:

  • "Spacious Wellfleet Tree Top Log Cabin Great For Families And Reunions": Enjoy a week relaxing and unwinding at this fantastic escape in the middle of nature. Once you've reenergized, enjoy basketball or hiking and biking, which are among the fun activities in this region.
  • "Rustic Cozy Log Cabin": After a big day of trying out some local activities, such as snowboarding and fishing, return home to this charming property.

What are the top-rated vacation rentals for weekend getaways in or near Chatham?

There's nothing like squeezing in a quick break to reenergize your batteries. Pack your carry-on bag and catch your breath at one of these irresistible weekend getaways in and near Chatham:

  • Spend your whirlwind escape at "Exceptional - Waterfront Home", which is around 25 miles to the west of central Chatham. There's lots of adventure and nature to uncover here. Go mountain biking and kayaking or simply take in the sights of Tisbury Town Beach and Seagull Beach.
  • "Water View - Walk Town/beach, Pets Considered" is another great property to consider. Around 1 mile south of Chatham, use it as a base to enjoy some horse riding or basketball. Red River Beach and Thumpertown Beach also have to be on your must-do list while you're here.

Can I find studio apartments for rent in and around Chatham?

Typically compact, less expensive and well located, it's difficult not to succumb to the charms of a studio apartment. Escape to one of these options and get to know Chatham up close:

  • Explore the world around you and then sleep soundly at "Luxurious Harbor View “eliza” Cottage Next To White Elephant". This property is a wonderful base for seeing the sights and offers amenities including a fitness facility and towels.
  • Another inviting choice is "Bright, Comfortable 1 - Bedroom". Take advantage of nearby whale-watching activities, a fridge and other conveniences during your vacation.

There are lots of attractions around Chatham to add to your itinerary. Feed the culture lover in you and visit Outpost 186 and The Company Theatre.

Can I find short term rentals in or near Chatham?

Every now and then, you just need to escape from it all, even if it's only for two or three days. Experience a nice mix of relaxation and sightseeing at one of these short-term rentals in or around Chatham:

  • If you want to be near the action, "Located Steps Away To Main Street And. 7 Miles From Surf Drive Beach" will suit your style. It's within easy reach of the heart of Chatham and a handy base to explore attractions like Walden Pond and Louisa May Alcott's Orchard House.
  • Eat, sleep and explore what's around you from "Water View - Walk Town/beach, Pets Considered", another terrific option. Old Manse and Concord Visitors Center should be on your must-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Chatham?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a fantastic way to say "I love you." Whisk your special someone off for a couple of days at one of these popular escapes in or near Chatham:

  • Put on some soft tunes and slow dance the nights away at "Luxurious Estate Includes - Tennis Court". Around 25 miles from Chatham, this property has all you need for a couple's weekend away, including a nearby bay and a fireplace.
  • Alternatively, spend your escape sipping wine and canoodling at "Oceanfront Contemporary Home - Breathtaking Views", around 25 miles from Chatham. Winery tours and a fireplace will help set the scene for romance.

Are there mansions for rent in or near Chatham?

We've got some awesome mansions for rent in and around Chatham. If you want somewhere with ample space as well as a large dose of wow factor, these architectural stunners will not disappoint:

  • Around 15 miles to the west of Chatham is "West Yarmouth Waterfront Mansion Right On The Ocean With Million". As well as its awe-inspiring design, you'll also love its first-class amenities, such as a fireplace and a garden.
  • Alternatively, take your vacation up a notch and spend a few days at "Prestigious Monomoy Mansion With Heated Pool And Provence Flair". It's located 30 miles to the south of Chatham and offers amenities like a swimming pool, a fireplace and more.

What are the best large group vacation rentals in or near Chatham?

Big groups mean big fun. They also mean finding a place that'll comfortably fit your whole crew. Browse our large group vacation rentals in or around Chatham and get your favorite people together under the same roof:

  • A great range of amenities including a swimming pool and a garden make "Luxurious Estate Includes - Tennis Court" a favorite. This spacious getaway has 6 bedrooms and sleeps up to 14 guests. From the heart of Chatham, it's around 25 miles away to the west.
  • Nothing's more important than being with the people you love, and "Water View - Walk Town/beach, Pets Considered" makes it easy to do that. Located around 1 mile to the south of Chatham, as many as 14 guests can stay in this vacation rental which has 5 bedrooms. A swimming pool and a water view are among the many amenities on offer here.

What are the best houses for rent with a pool in or near Chatham?

A pool is often an all-important amenity when choosing where to spend your vacation, particularly if you're traveling with kids. Browse these houses with a pool in or near Chatham and fill your days with laughter and fun:

  • Welcome to "New House, Steps To Beaches, Main St", where your biggest priority will be relaxing by the pool. Amenities including free toiletries and outdoor furniture help make this retreat a guest favorite.
  • "Hóll Adventure House - Perfect For Groups" is the type of place you go to get away from everything and appreciate your surroundings, starting with its awesome pool. A kitchen and childrens activities are also on hand to make your visit a memorable one.

Wondering what the weather's like in Chatham? It has a humid subtropical climate, with average temperatures in summer ranging from 65 ºF to 70 ºF. If you're chasing more inspiration on places to stay in this popular destination, use the search bar at the top of the page and adjust the filters to look through our entire selection of Chatham vacation rentals.