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Chatham vacation rentals

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Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Chatham vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Stay near Chatham's top sights

Chatham Bars Inn97 locals recommend
Wequassett Resort and Golf Club59 locals recommend
Chatham Lighthouse105 locals recommend
Ridgevale Beach21 locals recommend
Chatham Pier Fish Market77 locals recommend
Chatham Squire140 locals recommend

Chatham house rentals

Guest favorite

Home in Chatham

4.9 out of 5 average rating, 115 reviews

Cute cottage walking distance to Ridgevale Beach

Guest favorite

Home in North Truro

4.98 out of 5 average rating, 266 reviews

Beautiful North Truro cottage with screen porch

Guest favorite

Home in Harwich

4.98 out of 5 average rating, 496 reviews

cape cod riverview cottage

Superhost

Home in Chatham

4.96 out of 5 average rating, 116 reviews

Summerfell Cottage close to Ridgevale Beach

Guest favorite

Home in Yarmouth

5.0 out of 5 average rating, 101 reviews

Best of Yarmouth | Spa & Outdoors & Entertainment

Guest favorite

Home in South Yarmouth

4.93 out of 5 average rating, 211 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

Guest favorite

Home in Yarmouth Port, Cape Cod

4.99 out of 5 average rating, 315 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

Superhost

Home in Chatham

4.83 out of 5 average rating, 59 reviews

Walk to beach! Chatham Luxury near downtown, CBI!

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Chatham cottage rentals

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 147 reviews

140 Steps to Beach with Water Views

Guest favorite

Cottage in Chatham

4.94 out of 5 average rating, 147 reviews

Cape Cod Classic Cottage Near Forest Beach

Guest favorite

Cottage in Chatham

4.9 out of 5 average rating, 128 reviews

Forbes, a South Chatham cottage

Guest favorite

Cottage in Yarmouth

4.92 out of 5 average rating, 415 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

Guest favorite

Cottage in Yarmouth

4.99 out of 5 average rating, 176 reviews

Serenity Views | Waterfront | King | Firepit Kayak

Guest favorite

Cottage in Wareham

4.97 out of 5 average rating, 264 reviews

Cottage on Sunset Cove

Guest favorite

Cottage in Eastham

4.91 out of 5 average rating, 191 reviews

Classic Cape Cod Cottage

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 104 reviews

Steps to the Beach Kid Friendly

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Other great vacation rentals in Chatham

Guest favorite

Guesthouse in Brewster

4.94 out of 5 average rating, 214 reviews

Charming Antique Cape Cod Cottage

Guest favorite

Condo in Brewster

4.88 out of 5 average rating, 175 reviews

Shining Sea Condo

Guest favorite

Guest suite in Chatham

4.94 out of 5 average rating, 147 reviews

The Captain Kimball House of Christmas Joy

Guest favorite

Condo in Dennis

4.99 out of 5 average rating, 173 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 129 reviews

Modern Luxury Apt. | 7 min from Commons

Guest favorite

Place to stay in Wellfleet

4.97 out of 5 average rating, 175 reviews

WoodsideTiny House near Wellfleet Bay

Guest favorite

Apartment in Chatham

4.97 out of 5 average rating, 235 reviews

The Knoll

Guest favorite

Apartment in Chatham

4.93 out of 5 average rating, 203 reviews

Charming Downtown Chatham Apartment

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Quick stats about vacation rentals in Chatham

  • Total rentals

    540 properties

  • Rentals with a pool

    30 properties have a pool

  • Pet-friendly rentals

    170 properties allow pets

  • Family-friendly rentals

    450 properties are a good fit for families

  • Total number of reviews

    15K reviews

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Chatham?

    Yes! Work meets play with ease at over 210 vacation rentals in Chatham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chatham?

    Four-legged friends are welcome in Chatham. Choose from more than 170 vacation rentals for guests traveling with pets.

  • Are there Chatham vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Chatham, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Chatham?

    Experience the best of Chatham with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chatham have a bbq area?

    Absolutely! We offer over 260 house rentals with a bbq area in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Chatham have wifi?

    Absolutely! We offer over 40 cottage rentals with wifi in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Chatham have air conditioning?

    Absolutely! We offer over 30 cottage rentals with air conditioning in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chatham have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Chatham?

    Chatham has more than 30 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Condo Rentals in Chatham?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore