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10 Best Vrbo Vacation Rentals In Chatham, Massachusetts - Updated 2021

vrbo cape cod chatham

When in Chatham, the beaches are unmissable. Make sure you head to Lighthouse Beach, Harding Beach and Oyster Pond Beach. But there’s plenty more to do besides the beaches and seafood too! Rent bikes and explore bike paths along the Cape, spot seals playing in the water by the Chatham Pier, go shopping on Main Street, catch a movie at the Orpheum theatre. As for the lighthouse, consider moving over the obvious Chatham Lighthouse and head over to the Stage Harbour Lighthouse which is even more impressive. In Chatham, you have plenty of vacation rental options to choose from ranging from small bungalows to beach mansions, depending on your budget and preferences. Also, the closer you are to the water and the time of the visit may significantly impact your costing too. We’ve curated some of the top accommodation choices for you. Check out the best Vrbo accommodations in Chatham, Massachusetts here.

1. Oceanfront house within walking distance of beaches and town (from USD 700)

This 2400 sq ft (222 sqm), four-bedroom house has an ocean harbor seafront with private stairway access to the harbor and lovely elegant interiors. Perfectly seated on the bank with the backyard overlooking the harbour coupled with unobstructed views of both Little Mill Pond and Mill Pond, the views from the house are truly spectacular. It’s also an easy walk to Lighthouse Beach or Andrew Hardings Beach and Chatham’s Village which houses shops and restaurants. The house has been recently renovated and comes with a well-appointed full kitchen, centralized air-conditioning, gorgeous wood flooring, and a brick-walled patio.

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
47 reviews
House 12 Guests 4 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
Kitchen was clearly the gathering place with dining room just off it which had a wonderful view of bay
The outdoor space is as lovely as the spaces indoors
The fact that you can walk to town made it extra special
The home is close to everything town beach
We were 8 adults and a 2 month old attending a family wedding
It was spacious and exactly as listed
The property is nicely decorated very clean and well maintained
The owner had a booklet of information waiting for us about the particulars of the home Great spot David
were very helpful and accommodating when we requested to arrive early/check out late and sent over a ton of helpful information
and we really grew to love the home
great views make for a good time
They allowed full access to their home beach chairs etc quickly answered any questions we had by email sent a detailed info packet on Chatham restaurants beaches etc that proved to be very...
but yet it is in a secluded quiet neighborhood
It's steps away from Main Street where all the stores and shops are
Also this property is a (very) easy walk into the best shopping area of Chatham and also to the beach and lighthouse area
The house is only a 5 min walk to town
Chatham is a lovely little town full of shoppes art galleries and restaurants
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2. Bright and beautiful single-story, two-bedroom townhouse (from USD 160)

This property is a bright and beautiful two-bedroom townhouse spanning 1200 sq ft (111 sqm) The house has been newly renovated and features an open floor plan, vaulted beam ceilings, a built-in gas fireplace, and hardwood floors. The well-equipped kitchen has granite counters, tile backsplash, a dishwasher and a large island with seating for four along with an adjacent dining area with a large table perfect for meals and playing board games. The outdoors includes a patio with ample seating, a gas grill and atmospheric string lights coupled with an outdoor shower. The place is located near the shops and dining areas of Chatham, 0.5 miles (0.8 km) from Oyster Pond and 2 miles (3.2 km) from Lighthouse Beach.

Newly Renovated! Walk to Beach and Town!
16 reviews
townhome 7 Guests 2 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
It was great to be able to watch the Celtics game in the TV room while I was cooking in the kitchen
Had everything we could have wanted
The outdoor patio was a bonus as well
We enjoyed the comfy beds and quiet area
The house was beautifully decorated and up-to-date The large table in the kitchen was a perfect fit for me and my 6 friends
The house was clean and slept 5 adults comfortably
The hosts are responsive and gracious
Great amenities Back deck with outdoor shower
Everything about the property was wonderful
Beautiful rental home with wonderful patio for relaxing or having a barbeque
We all felt very relaxed safe and comfortable there and it made a great home base for travel around the Cape
It's conveniently located to so many great places in and near Chatham
location was great; a few minutes walk to Main Street but removed enough for a relaxed/quiet retreat Already looking at dates for next year
The location is ideal for walking--close to food downtown Chatham and a family beach
It is in a great location to walk to town and also an easy drive to other nearby towns
so we were able to walk or ride bikes any and everywhere
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3. Dog-friendly waterfront property with two decks (from USD 428)

Featuring expansive views of Pleasant Bay, two decks, two living areas, and four bedrooms, this vacation rental has plenty of room and is an ideal choice for a peaceful retreat with family or a large group of friends. The property is also dog-friendly and you don’t need to leave your furry family member behind either. The living space features ample seating and is in the center of the home with two bedrooms on each side. The bedrooms are spacious and feature plenty of natural light. The deck and porch have plenty of outdoor furniture, tables for alfresco dining, a hammock and a gas grill. The kitchen is well-appointed with all the equipment and paraphernalia you may need.

Walk to Beach- Water Views-Pet Friendly -A/C- Private location- Welcome to Waterfront
1 review
House 10 Guests 4 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
The house is quite large and there was plenty of room for everyone with a lovely living room great TV room and even a formal dining room
WIth two bedrooms on one side of the house and two on the other
The bedroom settings worked so well for us because some like to rise very early and some liked to sleep in
We spent a lot of time out on the deck which even had awnings for shade and rain protection
My childhood friends and I spent a fabulous week in this wonderrful home right in the middle of the Cape
The location is very quiet and not far from lovely downtown Chatham with wonderful shops and restaurants Centrally located for trips to the boat docks in Hyannis and Provincetown
The setting of this house is incredible with beautiful views of Pleasant Bay from most of the windows in the house
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4. Four-bedroom house with stylish interiors, private yard and water views (from USD 356)

This four-bedroom property is a comfortable family home sitting near the end of a quiet dead-end road. Located just five minutes’ from the Ridgevale Beach and a quick drive to Downtown Chatham or Harwich Port, this home can comfortably sleep up to eight people. The main floor has a wide open floor plan with two separate living areas, one bedroom with twin beds, a well-equipped kitchen, and a dining area. It also comes with a large deck to enjoy lovely views of Buck’s creek while just taking in the sunset or barbecuing. The second floor has three bedrooms - one with a king size bed, one with a queen size bed and one with twin beds. The house comes with a large private yard and an outdoor shower. The house is centrally air-conditioned, has laundry equipment in the basement, is Wi-Fi enabled and allows dogs.

#611: Stunning water views, 2 decks, walk to Ridgevale Beach, dog friendly!
16 reviews
House 8 Guests 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The four bedrooms accommodated us nicely and the spacious living spaces were perfect
It did have an ant problem
The house itself sleeps 6 in bedrooms upstairs with a daybed and trundle bed downstairs
but it was addressed promptly once we notified Del Mar
At the end of the street with the estuary on two sides and the ocean behind the other side of the street
The house was spacious and clean great amenities
it was extremely quiet and felt secluded
The street was delightfully quiet and the views were amazing
We've been going to Ridgevale beach for years with it's warm calm estuary waters opposite the ocean side and expansive tidal flats for the kids to explore
The home was ready and the condition was as advertised
They had a maintenance guy come the day after to spray around the perimeter
Del Mar has been great and super responsive and we will definitely rent from them again
But the views make all the difference with a wonderful back deck looking out over the marsh and a roof deck off the master
This house is just a five minute walk from the beach and easy driving distance to Chatham center and Rt 28 businesses
This was a beautiful property and very convenient to the beach (less than 5 minute walk)
The house is perfect for one or two families looking for gorgeous views within walking distance to the best family beach on the cape
After spending one week with my sisters in this old captain's home with a widow's walk and beautiful deck and being able to just take in the serenity of it's location
The scenic views of Bucks Creek changed throughout the day with the tides a delight to watch from the outdoor patio the roof deck and even from inside An easy and pleasant walk to Ridgevale Beach
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5. Furnished property in a townhouse complex with tennis court, swimming pool shared access (from USD 500)

This 2500 sq ft (232 sqm) picture-perfect townhouse is set on 17.5 acres (7 hectares) and is beautifully and meticulously designed for the best of style and comfort. The elegantly furnished house features four bedrooms, a spacious area, dining space for eight, a well-appointed kitchen with an island and breakfast bar and luxury bathroom fittings. The guests at the property have access to the tennis court, swimming pool, huge lawn and more. There are also plenty of excellent restaurants nearby, ranging from casual to fine dining, for when you do not wish to cook. The location also puts you in close proximity of Chatham Main Street’s eclectic shopping options, sightseeing, whale watching, golf, movies, concerts and more.

New Waterfront Townhome
7 reviews
House 10 Guests 4 Bedrooms 5 Bathrooms
Top guest reviews
Amenities & Room:
We were greeted by the property manager and shown all the amenities- all the way to the boats for our use on the water
The setup was ideal for traveling with multiple family members and young children as there was plenty of space and beds for everyone to feel comfortable
The house is stocked with supplies -- so all you really need to bring is yourself and your clothing
very attentive and responsive Three generations combining a vacation with a family wedding nearby completely enjoyed this spacious and comfortable vacation home
We could not have been happier with our stay- the "townhouse" was really a beautifully decorated and maintained home with an unbelievable location
We rented all three townhouses for a family reunion
Beautiful location Grounds meticulously cared for and pool was delightful
Our family had a wonderful vacation and would definitely come back
a picturesque corridor with great shops restaurants and bars
Beautiful property - well appointed and close to beaches and Main Street in Chatham
There is a great view from this Townhome and Oyster Pond itself is pristinely manicured and a gorgeous setting for anybody looking to partake in swimming fishing tennis or just relax
It's a very quick drive to the heart of downtown Chatham
it was like staying in a spread from a high end design magazine
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6. Beautiful townhouse with two bedrooms and in proximity to all attractions (from USD 220)

This beautiful townhouse sits on the main street and is close to all of downtown’s attractions. It comes with two master bedrooms and additional sleeping arrangements in the living room. The house features air-conditioning in each room, heating, Wi-Fi access, and laundry equipment. Indoor entertainment options include a television, a DVD player and a book collection. The outdoors comes with a sun deck, a barbecue grill and a provision for alfresco dining. The place is only a short walk to restaurants, shops, Oyster Pond Beach, the movie theatre, a baseball field, and the village market.

Beautiful Townhouse in downtown, walk to restaurants, shops & Oyster Pond
57 reviews
townhome 6 Guests 2 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
kitchen and living room were all
I enjoyed sitting in the living room
the kitchen and living area provided great spaces for fun conversations
Kitchen was well stocked and the living room was a comfortable place to relax in Being able to walk to town for dinners and shopping
so we each needed our own bed/bath space for dressing
The home was clean and spacious for us
It's initial appeal of having 2 MBR w/ en suites
so the two large bedrooms with bathrooms was great
was perfect for us and the other couple we traveled with
Communication was good for planning and arrival
And since we had several events to attend we really appreciated the closet space and the proximity to all those events
Very clean comfortable well equipped and
Lilly and Mark were so accessible and accommodating which made our stay very comfortable
Also many levels to retreat to Walking distance to everything in Chatham Loved the location
Perfect location to enjoy Chatham and Cape Cod
This a great location also as it was so easy to get to different places of interest on the Cape
We saw the beautiful sunset from up there Walking distance to the super cute Main Street area of shops and restaurants Just so lovely driving around Chatham and looking at the lovely houses too
locally eating jam doughnuts at Chatham Village Cake and Bakery only a couple of minutes walk away After driving around Cape Cod and getting to know it better
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7. Three-bedroom house with a private beach (from USD 1842)

This 1900 sq ft (176 sqm) home is seated on its own private beach and offers unobstructed views of Pleasant Bay and the open ocean beyond. It’s also only a five-minute walk to the dozens of shops, restaurants and art galleries that line the main street. Also, the world-famous Chatham Bars Inn and Spa is only 200 yards (182 m) to its north. The house features three bedrooms and can house up to seven people comfortably. Each of the bedrooms has full-on ocean views and the outdoors have plenty of seating and a provision for alfresco dining.

Direct Ocean Front - Private Sandy Beach - 5 Min. Walk to Town
166 Shore Rd
House 7 Guests 3 Bedrooms 3 Bathrooms

8. Large vacation home on Morris Island, close to the best of nature (from USD 714)

large vacation home on morris island, close to the best of nature
Source: www.vrbo.com

This vacation home is located on 2 acres (0.8 hectares) of a prime oceanfront real estate on Morris Island. Offering panoramic views of the Nantucket Sound and Monomoy Islands, the sunsets from here are truly sublime. The house spans 5000 sq ft (464 sqm) and hints at Asian-style decor. With five bedrooms, three bathrooms, two powder rooms, and multiple living and dining spaces, it comes with plenty of space to accommodate larger groups up to 13 people. The outdoor space features sun loungers, a barbecue, a fire pit and plenty of seating with a provision for alfresco dining. Wake up to the sounds of songbirds and the sight of whitetail deer gracefully moving through the grass then head on to hike on the Monomoy National Refuge trails.

Oceanfront Luxury Home
Chatham, MA, US
9 reviews
House 13 Guests 5 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the views are breathtaking and the home very comfortable
the kitchen was great with everything you need to feed such a crowd including an outdoor bbq grill
master bedroom was like an apartment occupying the entire third level
overall this was a great property great location and we would revisit in a heartbeat
our family loves walking the beach and a 4 mile beach walk is at your backdoor
Read more reviews

9. Cozy, one-bedroom vacation rental for a couple (from USD 225)

This vacation home is a one-bedroom rental cottage with tasteful nautical decor that’s perfect for a couple’s retreat or a small family getaway. With breathtaking views of the Oyster Pond and the town beach just a short walk away, water babies will love the place. The sleeping arrangements include a king bed in the master bedroom and a pullout bed in the living room. The cozy living room features plush couches and a flat-screen television as well. The house comes with central heating, Wi-Fi access and shared laundry machine access. The outdoor area comes with a private furnished patio and a gas grill.

Chatham Windmill Cottage w/ Oyster Pond Views!
28 reviews
cottage 3 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The accommodation is very comfortable with off road parking lounge and combined kitchen
The cottage is very quirky and comfortable with all you might need
The space was immaculate well equipped and very cozy
The Wi-Fi and Cable TV worked well
The house is cozy charming and very comfortable
Everything I had pictured and more
So clean and very nicely decorated
and we also used the laundry facilities (in the garage) - it sure beat having to sit in a laundromat
the owner was charming and dealt with our questions very promptly as well as being very flexible
so that was not a problem for us
Linda was a great host and even made sure a snow plow came the morning after a snow storm
The interior is beautifully decorated and spotless and made us feel right at home
She gave us great recommendations on where to eat and where to go if we wanted to venture out of Chatham
We were minutes from shops and restaurants and coffee and just a 10 minute walk to the beach
We booked this last minute looking for a close to town location
Wonderful setting location could not be better & cottage
The location is ideal: Set in a garden of a residential upscale neighborhood; quiet but close to the village and shops overlooking the beautiful Pond
Chatham is a great little town with lots of shops and great food in walking distance of the cottage
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10. Four-bedroom, pet-friendly property with huge backyard, garage and workshop (from USD 929)

four-bedroom, pet-friendly property with huge backyard, garage and workshop
Source: Vrbo

This 3000 sq ft (278 sqm) property is located on the ocean side of Shore Road with an easy walk to four of Chatham’s swimming beaches, the fish pier, restaurants and more. It features four bedrooms, a full kitchen, a garage, a workshop and a huge backyard with organic vegetables and a flower garden. The outdoors also come with chairs to relax and unwind at the end of the day while enjoying a drink. Entertainment options include a television, a book collection and close proximity to golf and tennis facilities. Pets are allowed on this property.

Shore Road Luxury Home with Ocean Rights
Chatham, MA, US
9 reviews
House 8 Guests 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
Five adults shared the home enjoying evening fires
its not appointed like a rental
However the master suite was very nice
Cape Cod memories were made for my children here in one of the most beautiful settings imaginable
The house had everything we needed as far as amenities go was very spacious for 6 adults and 3 kids
It was clean and roomy and very comfortable
the owner is a delight to work with and provides many helpful tips
This is a great vacation home and the owners could nt have been more attentive Great place
My teenagers thought she was haunted and loved exploring
Cod memories so precious to all of us
We were late getting there because of our flights and the owner had breakfast items delivered for us
We also walked to the Chatham baseball games AWESOME Very close to the Chatham Pier Fish Market and the wonderful Chatham Bars Inn Robert
and we loved being able to walk to the center of town multiple beaches and the Chatham Bars Inn Resort
Everything provided An absolutely beautiful garden Walk to beaches restaurants and the center of the charming village
The grand old lady was very eccentric and quirky
We enjoyed an exceptional week in this most special home Character and charm without sacrificing modern comforts Walk to a private beach using a secret passage through the garden or stroll to ma...
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Explore the architecture and homes in Chatham

Chatham is home to some mansions that can rival even the best European chalets. Spend some time strolling around and check out some truly spectacular seaside homes.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Mehak is a young student from India majoring in Finance. Travelling is something that has always fascinated her, she intends to solo travel the world. She enjoys reading about anything and...Read more

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