What are some interesting places to visit in or near Chatham, MA?

Chatham is full of charming spots! You can visit the Chatham Lighthouse, a historic landmark with stunning views, or explore the Chatham Historical Society Museum to learn about the town's rich history. If you're a nature enthusiast, head to the Chatham Bars Inn Beach for a relaxing day by the sea, or take a walk through the scenic Chatham Cranberry Bogs.

What are the best Airbnb and holiday rentals in Chatham, MA?

In-town - Pied-a-terre - Private - Sunny Comfy Home , Chatham Walk To Cape Cod Beach and The Secret Garden are among the best Airbnb and holiday rentals in Chatham, MA.

Which walking or cycling routes are the best in Chatham, MA?

The Chatham Rail Trail is a great choice for both walking and cycling, stretching along the former railroad line. If you're looking for a more scenic route, try the Chatham Coastal Trail, which offers beautiful views of the Atlantic Ocean. For a shorter walk, explore the Chatham Light Beach, a lovely stretch of sand with the iconic lighthouse in the background.

What are the most popular Airbnbs in Chatham, MA?

Among the Airbnbs in Chatham, MA, In-town - Pied-a-terre - Private - Sunny Comfy Home , Chatham Walk To Cape Cod Beach and The Secret Garden are the most popular ones.

What sports or outdoor activites can visitors enjoy in and around Chatham, MA?

Chatham is a haven for outdoor enthusiasts. You can enjoy swimming, sunbathing, and surfing at the many beaches, like Lighthouse Beach and Hardings Beach. For something more adventurous, try kayaking or paddleboarding in the calm waters of Stage Harbor. If you're visiting in the winter, don't miss the chance to go ice skating at the Chatham Municipal Rink.

What are the best holiday rentals with a pool in Chatham, MA?

Lucky Number Seven , Beach Chic Chatham 5 5min's Walk To Private Beach-newly Renov'd Family Retreat and Charming Walk To Beach Chatham-bayview Beach House--central A\/c; Wi-fi are the best holiday rentals with a pool in Chatham, MA.

What other towns or cities can be easily accessed from Chatham, MA?

Chatham is conveniently located near other charming towns on Cape Cod. You can easily drive to nearby towns like Harwich Port, Dennis, and Orleans, each offering its unique charm and attractions. For a slightly longer drive, you can visit the bustling town of Hyannis, known for its ferry service to the islands and its vibrant nightlife.

What are the best rentals for families and kids in Chatham, MA?

The best rentals for families and kids in Chatham, MA are Chatham Walk To Cape Cod Beach , Tranquil Cape Cod Getaway - chatham and Slate House - A Modern Waterfront Getaway .

What amenities are commonly available in vacation rentals in Chatham, MA?

Vacation rentals in Chatham typically offer a range of amenities, from fully equipped kitchens and comfortable living spaces to outdoor decks and patios. Many rentals also include amenities like laundry facilities, Wi-Fi, and cable TV. Some rentals even offer extras like private pools, hot tubs, and fireplaces.

What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?

The best holiday rentals or Airbnb with a jacuzzi in Chatham, MA are Slate House - A Modern Waterfront Getaway , Perfect For Group W\/ Kids & Dogs W\/ Hot Tub and Great Location - Water View - Walk To Beach & Town .

What time of year is best to rent a vacation rental Chatham, MA?

The best time to rent a vacation rental in Chatham depends on your preferences. Summer is the peak season, offering warm weather and plenty of outdoor activities. Spring and autumn provide a more relaxed atmosphere with pleasant temperatures and fewer crowds. If you're looking for a winter escape, Chatham offers a charming and peaceful experience with opportunities for winter sports.

Chatham, MA Holiday Rentals and Airbnb

10 7 reviews

Dog Friendly, Game Room, Central Ac!

apartment, Chatham

This 3-bedroom, 3-bathroom flat, sleeping up to 8 guests, is situated in Chatham's Sandy Buoys district, offering excellent access to local attractions and the picturesque beaches of Cape Cod.
This pet-friendly accommodation includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, on-site parking, a garden, and a game room for entertainment.

9.9 59 reviews

Chatham Beach Cottage

house, Chatham

This two-bedroom cottage is situated in Chatham, just 0.5 kilometres from the beach and a short distance from the town centre and Cockle Cove on the Nantucket Sound.
The cottage offers a full kitchen, a private patio, and an outdoor shower, providing a relaxing retreat for up to five guests.

9.4 99 reviews

Chatham Village - Adorable Studio Apartment In Antique Home

studio, Chatham

This Chatham apartment, less than 1.6km from Mayo House and Cape Cod beaches, offers easy access to local attractions including the Chatham Windmill and Atwood House Museum, all within a 24km radius.
The self-catering flat features one bedroom, one bathroom, sleeps two guests, and includes a kitchen with fridge and microwave, a terrace, free Wi-Fi, a parking space and access to a spa.

9.2 57 reviews

South Chatham Sunshine

house, Chatham

This three-bedroom house is located in South Chatham, a short distance from Ridgevale Beach (2.4 kilometres), Cockle Cove Beach (2.6 kilometres) and Forest Beach, all within a 10-minute walk.
The 138 square metre property features a fully equipped kitchen, a patio, a garden and parking, ideal for families or groups looking for a comfortable and convenient base to explore Chatham.

9.8 141 reviews

Private Beach In Chatham - Sleeps 5

apartment, Chatham

This Chatham beachfront apartment offers direct access to a private beach, is less than 1.6km from Chatham town centre with its shops and restaurants, and a short walk from Chatham Lighthouse Beach and the Monomoy National Wildlife Refuge.
Sleeping five comfortably, this two-bedroom, one-bathroom property features a king-size bed, full-size bed, and twin bed, a fully equipped kitchen, keyless entry, Wi-Fi, two parking spaces, and access to an outdoor dining area with a Weber gas grill and an enclosed outdoor shower, plus a fitness centre.

9.2 5 reviews

Charming Updated Home In Chatham

house, Chatham

This Chatham holiday home is an 11-minute walk from Forest Beach and 2.1 km from Red River Beach, conveniently located near Nauset Lighthouse (24 km) and Wellfleet Bay Wildlife Sanctuary (34 km).
The 169 square metre property boasts four bedrooms, two bathrooms, and sleeps up to 15 guests, offering a fully equipped kitchen, free Wi-Fi, and a private patio; guests under 25 must be accompanied by an adult.

10 63 reviews

Modern, Newly Renovated, 3-bed Peach Tree House

apartment, Chatham

Chatham's Peachtree Cottage, a newly renovated three-bedroom cottage, is situated on a quiet residential cul-de-sac near cranberry bogs, 1.6 km from Ridgevale Beach and 4 km from Chatham's Main Street.
This 100 square metre property boasts a spacious sunroom, fully equipped kitchen, private fenced backyard with deck and outdoor shower, sleeps five guests, and includes high-speed internet, air conditioning, and parking for three cars.

9.4 88 reviews

Pond Front Home W/ Game Room Dog Friendly!

apartment, Chatham

This charming house is located just 0.5km from Adventure Chatham and within 5km of the Chatham Chamber of Commerce and Cape Cod Beaches, offering easy access to the area's attractions. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The house spans 223 square metres and comfortably accommodates up to 10 guests. It includes a fully equipped kitchen, a private garden, a gas grill, and a TV for entertainment, making it a perfect choice for families or groups seeking a relaxing and comfortable stay.

9.9 91 reviews

Central Ac Close To Beach Dog Friendly!

apartment, Chatham

This Chatham seaside property, situated within 3.2km of Hardings Beach and Cape Cod Beaches, and 4.8km from Ridgevale Beach, offers easy access to local attractions including the Chatham Chamber of Commerce and Chatham Drama Guild.
The 111 square metre house features three bedrooms, sleeping up to eight guests, a fully equipped kitchen, private garden with gas grills, and a terrace; enjoy sea views and the convenience of on-site parking.

9.4 109 reviews

Spacious W/ Large Outdoor Area Fire Pit!

apartment, Chatham

This seaside property is situated near Chatham, less than 1.6km from the Chatham Shark Center and Veterans Field, and within 3.2km of Gallery Antonia and Mayo House.
This 186 square metre house, sleeping eight guests, boasts four bedrooms, two bathrooms, a fully equipped kitchen, garden, terrace, parking, and in-house laundry facilities; enjoy ocean views and easy beach access.

9.4 53 reviews

Large Home W/ Fire Pit And Dogs Welcome!

apartment, Chatham

This spacious apartment is located in Chatham, just 1.1 kilometres from Goose Pond and a short drive to the bayside beaches. The property boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The apartment offers 164 square metres of living space, comfortably accommodating up to 10 guests. The property includes a fully equipped kitchen, a living room, a TV room, a garden, a terrace, parking, and a range of amenities such as a fire pit, a propane grill, and a washer and dryer, making it ideal for families or groups of friends.

9.8 149 reviews

Cute Cottage - Walking Distance To Ridgevale Beach

apartment, Chatham

This charming cottage is situated in a peaceful residential neighbourhood in Chatham, just 300 metres from Ridgevale Beach. It boasts excellent user, location, and cleanliness ratings, making it a great choice for families or groups of friends.
The cottage has two bedrooms and can accommodate up to six guests, offering a comfortable and spacious layout. It is equipped with a fully-equipped kitchen, a washer and dryer, WiFi, and a range of outdoor amenities, including a gas grill, an outdoor shower, and a storage locker full of children's beach toys.

The Best Family-Focused Holiday Rentals in Chatham, MA

Give the kids instant backyard beach fun and plenty of room to unwind at spacious family holiday rentals in Chatham, MA.

9.6 377 reviews

Pleasant Bay Village Resort

resort, Chatham

The Pleasant Bay Village Resort is located in Chatham, Massachusetts, just 4 kilometres from the Chatham Railroad Museum and 3.2 kilometres from the Chatham Municipal Airport. The resort is a 4-star property that has received excellent user ratings for its location, cleanliness and overall experience.
The resort offers spacious rooms with floral décor and private patios. Guests can enjoy a range of amenities including a seasonal outdoor pool, hot tub, game room, playground, free Wi-Fi, laundry facilities, a fitness centre, a restaurant and room service.

9.8 93 reviews

Great Location Outdoor Space Dog Friendly

house, Chatham

This family-friendly four-bedroom detached house in Chatham offers 10-guest capacity and is situated a short distance from Harding's Beach and Oyster Pond, with local amenities such as Hey Joe & Jam for coffee and Kream & Kone for ice cream within easy reach.
This dog-friendly property provides a fully equipped kitchen, air conditioning, Wi-Fi, parking, and a spacious outdoor area with a fire pit and deck, alongside indoor entertainment like a ping-pong table, with sheets and towels provided.

9.8 30 reviews

Beautiful Home W/ Artistic Flair!

house, Chatham

This detached house offers a secluded setting on a private cul-de-sac in Chatham, directly bordering the Cape Cod Rail Trail, and is a short 1.9 kilometre drive from downtown Chatham and Forest Beach.
This family-friendly property accommodates up to seven guests with three bedrooms and three bathrooms, featuring a chef's kitchen, multiple living areas including a workspace, and outdoor amenities such as a farmers porch, deck with a grill, and an outdoor shower, with pets welcome for an additional fee.

9.4 69 reviews

Waterfront On Private Lake!

house, Chatham

This waterfront property offers direct access to Lover's Lake in central Chatham, with Jackknife Beach and Harding's Beach a short 5-minute drive away.
This 4-bedroom cottage comfortably sleeps 9 guests and features a newly renovated kitchen, a downstairs games room, and multiple outdoor seating areas, ideal for families seeking a lake and beach holiday.

Holiday Rentals with a Pool in Chatham, MA

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Chatham, MA.

No reviews

Luxury Home With Pool Hot Tub & Water View

house, Chatham

This luxury residence in Chatham Port is located 2.4 kilometres from Scatteree Beach and 22.5 kilometres from Nauset Lighthouse.
This spacious 361 square meter property accommodates up to 23 guests and features six bathrooms, a well-equipped kitchen with a dishwasher, oven, and microwave, air conditioning, a swimming pool, a hot tub, a garden, parking, free WiFi, and a fireplace, with an on-site water park and outdoor seating offering sea views from its patio.

8.4 6 reviews

Pool And Large Yard!

apartment, Chatham

This dog-friendly four-bedroom holiday home in North Chatham offers a private in-ground swimming pool and is conveniently located near Cape Cod Beaches and Cape Cod National Seashore, with the Chatham Railroad Museum and Chatham Marconi Maritime Centre also within easy reach.
This spacious accommodation comfortably sleeps nine guests and features central air conditioning, six televisions, Wi-Fi, a well-equipped kitchen with a microwave and dishwasher, and outdoor amenities including a gas barbecue and an outdoor shower.

10 2 reviews

Luxury Home With Pool, Hot Tub & Water View

house, Chatham

This luxury residence is located on a cove in Chatham, offering water views and a 10-minute drive to downtown Chatham's amenities.
This five-bedroom, five-and-a-half-bathroom property accommodates up to 12 guests, featuring a heated swimming pool, hot tub, gas fire pit, and a chef's kitchen, with proximity to Jacknife and Lighthouse Beaches.

10 15 reviews

Walk 2beach, Pool, Hot Tub, Gameroom, Petsok

apartment, Chatham

This four-bedroom apartment in Chatham is situated just a short walk from Hardings Beach, offering easy access to the beautiful coastline.
The 334.45 square metre property boasts a private pool and hot tub, a game room, a movie room, and an outdoor kitchen with a fire pit area, providing ample space and entertainment options for up to 10 guests.

Frequently asked questions about holiday rentals in Chatham, MA

What are some interesting places to visit in or near Chatham, MA?
Chatham is full of charming spots! You can visit the Chatham Lighthouse, a historic landmark with stunning views, or explore the Chatham Historical Society Museum to learn about the town's rich history. If you're a nature enthusiast, head to the Chatham Bars Inn Beach for a relaxing day by the sea, or take a walk through the scenic Chatham Cranberry Bogs.
What are the best Airbnb and holiday rentals in Chatham, MA?
In-town - Pied-a-terre - Private - Sunny Comfy Home, Chatham Walk To Cape Cod Beach and The Secret Garden are among the best Airbnb and holiday rentals in Chatham, MA.
Which walking or cycling routes are the best in Chatham, MA?
The Chatham Rail Trail is a great choice for both walking and cycling, stretching along the former railroad line. If you're looking for a more scenic route, try the Chatham Coastal Trail, which offers beautiful views of the Atlantic Ocean. For a shorter walk, explore the Chatham Light Beach, a lovely stretch of sand with the iconic lighthouse in the background.
What are the most popular Airbnbs in Chatham, MA?
Among the Airbnbs in Chatham, MA, In-town - Pied-a-terre - Private - Sunny Comfy Home, Chatham Walk To Cape Cod Beach and The Secret Garden are the most popular ones.
What sports or outdoor activites can visitors enjoy in and around Chatham, MA?
Chatham is a haven for outdoor enthusiasts. You can enjoy swimming, sunbathing, and surfing at the many beaches, like Lighthouse Beach and Hardings Beach. For something more adventurous, try kayaking or paddleboarding in the calm waters of Stage Harbor. If you're visiting in the winter, don't miss the chance to go ice skating at the Chatham Municipal Rink.
What are the best holiday rentals with a pool in Chatham, MA?
Lucky Number Seven, Beach Chic Chatham 5 5min's Walk To Private Beach-newly Renov'd Family Retreat and Charming Walk To Beach Chatham-bayview Beach House--central A\/c; Wi-fi are the best holiday rentals with a pool in Chatham, MA.
What other towns or cities can be easily accessed from Chatham, MA?
Chatham is conveniently located near other charming towns on Cape Cod. You can easily drive to nearby towns like Harwich Port, Dennis, and Orleans, each offering its unique charm and attractions. For a slightly longer drive, you can visit the bustling town of Hyannis, known for its ferry service to the islands and its vibrant nightlife.
What are the best rentals for families and kids in Chatham, MA?
The best rentals for families and kids in Chatham, MA are Chatham Walk To Cape Cod Beach, Tranquil Cape Cod Getaway - chatham and Slate House - A Modern Waterfront Getaway.
What amenities are commonly available in vacation rentals in Chatham, MA?
Vacation rentals in Chatham typically offer a range of amenities, from fully equipped kitchens and comfortable living spaces to outdoor decks and patios. Many rentals also include amenities like laundry facilities, Wi-Fi, and cable TV. Some rentals even offer extras like private pools, hot tubs, and fireplaces.
What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?
The best holiday rentals or Airbnb with a jacuzzi in Chatham, MA are Slate House - A Modern Waterfront Getaway, Perfect For Group W\/ Kids & Dogs W\/ Hot Tub and Great Location - Water View - Walk To Beach & Town.
What time of year is best to rent a vacation rental Chatham, MA?
The best time to rent a vacation rental in Chatham depends on your preferences. Summer is the peak season, offering warm weather and plenty of outdoor activities. Spring and autumn provide a more relaxed atmosphere with pleasant temperatures and fewer crowds. If you're looking for a winter escape, Chatham offers a charming and peaceful experience with opportunities for winter sports.

Popular destinations

Holiday Rentals with a Balcony in Chatham, MA

Wake up to the soothing sights and sounds of blue ocean waters directly from your private rental balcony in Chatham, MA.

9.7 120 reviews

Stellar Home With Hot Tub & Movie Room!

apartment, Chatham

This charming house is ideally situated in Chatham, just 3km from Veterans Field, Hardings Beach, and Cape Cod Beaches, offering easy access to the area's attractions. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for travellers.
The house spans 260 square metres and comfortably accommodates up to 10 guests in its four bedrooms and two bathrooms. Enjoy a range of amenities including a fully equipped kitchen, a jacuzzi, a garden, a terrace, and parking, perfect for relaxing and exploring the local area.

10 2 reviews