Chatham vacation rentals

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Top-rated vacation rentals in Chatham

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Guest favorite

Home in Chatham

4.96 out of 5 average rating, 105 reviews

Amazing Family Friendly in-town - Chatham 5bedroom

Located on a quiet street steps from Main Street in the heart of downtown Chatham, this property has more charm than you can imagine! A brand-new luxury kitchen, new baths, and central Air Conditioning! The side yard is quiet and offers a calming place to unwind. The house is an easy walk to the beaches, shopping, and restaurants. Movie theater and ice cream place is just a couple steps away. It doesn't get any closer and easier. Leave the car at the house and walk everywhere! Large dining table for 10 and all the linens provided too. Perfect place for your family vacation! You have 2 King beds, 6 Twins and a Futon. House has parking for three cars but no car is necessary you walk to everything. Four bedrooms are upstairs along with a nice reading nook that looks out above the front door. Downstairs is two generous size living rooms, both with flat screen TV's. Nice kitchen with Island and bar as well as a dining table for ten that sits in a lovely sun porch. Walk directly onto your own yard and enjoy a barbecue after walking home from the beach.. The house is all yours. I spend lots of time in Chatham during July, but may not be on the Cape much during August. Either way I'm always a phone call away. Main Street offers easy proximity to beaches and award-winning restaurants and shopping. The location, a few steps away from downtown Chatham, is unbeatable. It's a quiet and peaceful street, yet close to the downtown hustle and bustle. The side yard is peaceful and quiet. You'll love all the space this five bedroom home has to offer. The house has two designated parking spaces in the driveway. If you have compact cars, you might be able to squeeze one more in too. A third parking space is just alongside the fence, but keep it close to the curb so that the neighbors have enough space to pull out of their driveway. One of the things we really enjoy about our home is our setting within a neighborhood, where the neighbors are nearby. Please be considerate of your noise outside. At night, we make sure that things are quiet outside by 10:00 pm, and ask that you do the same. Also, please turn off all exterior house lights at the end of the night.

Guest favorite

Condo in Chatham

4.96 out of 5 average rating, 282 reviews

In-town, Pied-a-Terre. Private, Sunny Comfy Home.

Bright, Sunny, fabulous in-town location. CLEAN, SAFE & PRIVATE hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, business trips, overflow guests. Comfortably furnished, thoughtfully outfitted. Quality linens, duvet etc. Walk to restaurants, cafe/bakery, groceries, shops, ballpark, Oyster Pond Beach, CBI, tennis courts, bike path, bike rental, etc etc. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

Guest favorite

Guest suite in Chatham

4.99 out of 5 average rating, 203 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table, private access to the fresh water pond, outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Guest favorite

Cottage in Chatham

4.96 out of 5 average rating, 218 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property.

Guest favorite

Home in Chatham

4.95 out of 5 average rating, 244 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Guest favorite

Guest suite in Chatham

4.99 out of 5 average rating, 106 reviews

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 547 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Guest favorite

Home in Chatham

4.96 out of 5 average rating, 106 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 154 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Guest favorite

Guest suite in Harwich

4.94 out of 5 average rating, 227 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 144 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

Guest favorite

Cottage in Chatham

4.9 out of 5 average rating, 128 reviews

Forbes, a South Chatham cottage

This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only !

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

4.96 out of 5 average rating, 116 reviews

Summerfell Cottage close to Ridgevale Beach

5.0 out of 5 average rating, 30 reviews

CHATHAMS BEST! Oceanview&private beach! 5 bd,4 bth

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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
$40 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 condo rentals in Chatham?
Experience the best of Chatham with our condo rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Chatham have a bbq area?
Absolutely! We offer over 30 cottage rentals with a bbq area in Chatham. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chatham have wifi?
Absolutely! We offer over 10 condo rentals with wifi in Chatham. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Chatham have air conditioning?
Absolutely! We offer over 10 bed and breakfast 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 house rentals in Chatham?
Chatham has more than 390 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Chatham?
Enhance your stay in our House Rentals with the most popular amenities: over 410 homes with wifi, over 390 homes with air conditioning, over 10 homes with a gym, over 260 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Chatham vacation rentals

Top-rated vacation rentals in Chatham

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Chatham vacation rentals

Stay near Chatham's top sights

Other great vacation rentals in Chatham

Cottage in Chatham

Guest suite in Chatham

Guest suite in Orleans

Apartment in Chatham

Home in Chatham

Condo in Brewster

Guesthouse in Brewster

Home in Chatham

Other great vacation rentals in Chatham

Home in Chatham

Home in Chatham

Home in Chatham

Home in Chatham

Home in Chatham

Home in Chatham

Cottage in Chatham

Home in Chatham

Quick stats about vacation rentals in Chatham

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chatham?

Are there pet-friendly vacation rentals in Chatham?

Are there Chatham vacation rentals on Airbnb with pools?

How much does it cost to stay in condo rentals in Chatham?

Do cottage rentals in Chatham have a bbq area?

Do condo rentals in Chatham have wifi?

Do bed and breakfast rentals in Chatham have air conditioning?

Do house rentals in Chatham have a gym?

Are there family-friendly house rentals in Chatham?

What are the most popular amenities for House Rentals in Chatham?

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