1. New England Vacation Rentals and Property Management

    1. New England Vacation Rentals and Property Management

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    Chatham, MA

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    New England Vacation Rentals and Property Management

    4.2 (5 reviews)
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    Surfside Motor Inn - Room 209

    Surfside Motor Inn

    4.1(14 reviews)
    2.1 mi
    $$

    Surfside is a vibe. Super nice and cozy spot with a friendly atmosphere. Vicky and the rest of the…read morestaff are awesome and fun to chat with, and the common areas typically have approachable and interesting guests lounging around. Front yard is popular with the local bunnies if you're into that. The place also happens to be one of the best locations in town -- right at the midpoint between the ocean and a prime July 4 parade viewing area, and in easy walking distance to the local shops and restaurants. Great rooms as well; got sort of a rustic character but without sacrificing the general comfort, cleanliness, or essentials you'd expect from a high-quality chain hotel. Been coming here for years and highly recommend it. Photo taken just now while enjoying the ocean breeze on the porch swing before bed.

    One of the most unique places I have stayed in quite some time…read more First off, while it's not cheap, it's definitely way less expensive than everywhere else in the area - especially for having parking, being literally across the street from the beach, and being a 10-minute walk to the Main Street. You could park once and then not have to drive again for your time in Chatham. Also, it's very well equipped - the people who run the place know what people need for the beach and work hard to make it happen. There's towels, wagons, umbrellas and coolers. There's a communal fridge and an ice machine. There's a vending area for drinks and a continental breakfast and a wine hour. Also plenty of space for sitting outside and visiting with a view of the water. The beach across the street is really cute, too. The rooms themselves are quirky, but clean and workable with fast WiFi. The stairs are really steep so if you have any mobility issues at all I would recommend a first floor room. The bed was comfortable and the new AC was useful for blocking out next door neighbor noise. The bathroom was a bit weird - the sink counter was falling off the base a bit and the floor seemed soft/likely in need of replacement, but all was functional. The only really odd thing was that my room was next to a room which had a private bath not in the room but across the hallway, and the neighbors had both bathroom and bedroom doors open going back and forth as if it was their private area - I felt like I was intruding although I had to go through the hall way to enter and leave. However, it just added to the quirk!

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    Surfside Motor Inn
    Surfside Motor Inn
    Surfside Motor Inn - Room 209

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    Room 209

    Chatham Guest Rooms - Enjoy the spacious accommodations in a farmhouse from the 1770's that has been fully restored in the last 5 years.

    Chatham Guest Rooms

    5.0(5 reviews)
    0.1 mi

    A home away from home in Chatham:…read more We loved our recent stay in Chatham and especially staying at the Chatham Guest Rooms. We stayed in the upstairs 'Main Suite' which was spacious and comfortable for our family of 4! We really enjoyed having a full kitchen to cook in and a washer and dryer too! The apartment also came with everything we needed to enjoy the beach: chairs, towels, umbrellas, and a beach tote to carry everything in. This really came in handy! Danielle and Bob were very welcoming and created a lovely, thoughtful vacation get-a-way for their guests in a beautifully restored historic farmhouse! Thank you!

    If you're looking for quality lodging at an affordable price on Cape Cod, I highly recommend…read moreChatham Guest Rooms. This is a house about a mile down from downtown Chatham with three "guest room" options: the Main Suite, which has a full kitchen, the Garden Suite, which has a private deck and library, and the East Room, where we stayed: a room with a private bath, queen-sized bed, and large window seat overlooking the garden that fills the rear of the property. The rooms all come equipped with coffee makers, cube fridges, and a cupboard with cups, plates, coffee filters, and other essentials. The East Room is large enough for two people, nicely decorated, and appointed with a lovely antique armoire and flat-screen TV. It has exposed ceiling beams, a cool, soothing decor palette, and soft lighting. The bathroom is modern with a glass-walled shower. My only caution is that the queen-sized bed is very soft, so be aware of that if you prefer a firm mattress. I got a peek at the Main Suite, which is gorgeous, and though we went off-season I could tell that the garden would be beautiful come springtime. This is not a B&B, but there are several options for breakfast nearby, more than that in-season. The business is run by two personable locals, Bob and Danielle, who also run a neat antique map shop that's adjacent to the rooms. They are helpful, attentive, and full of suggestions for things to see and places to dine. They allowed us our privacy while being attentive to our needs and picking up the room, and they checked on us regularly to make sure we were comfortable. Chatham is a quiet, quaint town with friendly people--not funky, more of a get-away-from-it-all type of place. The Guest Rooms are about a mile down from Chatham's downtown, which has a great locally-owned bookstore (remember those?), a neighborhood theater, and a variety of restaurants and shops. The lighthouse and beach are down there as well and make for a pleasant walk after a meal. There's a grocery store and CVS nearby. Chatham's location in the "elbow" makes it ideal for venturing out to explore other parts of the Cape. If things get too sleepy for you, the energy of Provincetown is about 75 minutes north. Cape Cod Mall is a 20-minute drive away if you tire of cute, small, locally-owned businesses and just want Starbucks and a movie with Dolby Surround Sound. Finally, the price is good, especially for the Cape where even off season B&B's and inns can be pricy. The local guide Bob and Danielle gave us reported that the Guest Rooms are one of the most reasonably-priced accommodations in the area. The Main Suite was priced about the same as a 3-star hotel room in a city and had much more to offer. For what we would have paid to stay at a flea-bag hotel, we had a great experience in a clean, comfortable, personally-appointed setting. .

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    Chatham Guest Rooms - The 2 room Garden Suite includes a living room, private deck and separate entrance.

    The 2 room Garden Suite includes a living room, private deck and separate entrance.

    Chatham Guest Rooms - The owners look forward to sharing their knowledge of the area with you to ensure that you enjoy yourselves year around.

    The owners look forward to sharing their knowledge of the area with you to ensure that you enjoy yourselves year around.

    Chatham Guest Rooms - Each unit includes a sitting area, private bathroom, mini refrigerator and access to the gardens.

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    Each unit includes a sitting area, private bathroom, mini refrigerator and access to the gardens.

    Pilgrim Village - Real Sunset on pond

    Pilgrim Village

    2.3(3 reviews)
    0.2 mi

    My son is the 5th generation to stay at Pilgrim Village. That should tell you a lot- an ideal and…read moreaffordable setting for a family vacation located within easy walking or biking distance to a number of beautiful beaches, the town of Chatham, shopping and restaurants. Chatham is one of the last bastions of civilization. The town is beautiful, the people friendly, and everybody seems ecstatic to be there. The 4th of July parade is a real slice of Americana- a gesture back to a simpler time. I've travelled to almost every state and a long list of countries, but Chatham and Pilgrim Village top the list of places that make my blood pressure drop and a smile to my face. My 7 yr old son has a blast, and I feel comfortable that he is always safe riding his bike by himself through the community, meeting a bunch of kids his age, going to the playground or shuffleboard court. We never worry about him, and when we leave the community we don't even think about locking our cabin. The tranquil beach on White Pond has the cleanest water I've ever seen, is full of fish, rowboats are provided, and just sitting by it lowers your blood pressure by 30 points. If you want a 5-star hotel with mints on your pillow every night, this is not the place. But if you like a mildly rustic, relaxed atmosphere, a place where you can bring an entire family for a week for less than a thousand bucks a week, want the option to cook in your cabin rather than bear the expense of eating 3 meals a day at restaurants, this is the place for you. The Swenson family has run the place forever, are infinitely helpful, and really care about the beautiful grounds. Their daughter, son-in-law and son are taking over, and bringing new ideas to the mix like wifi, Sunday s'mores cookouts and 4th of July fireworks at the beach. One other reviewer spoke of the "draconian rules". I don't know what he was up to, but I've never experienced anything like that. If you are single, a couple, or a family, I highly recommend Pilgrim Village. Most of the visitors have made it a tradition. Many, like me, have been coming here for decades. We stay for 2 weeks each year. At this price, an extended stay is totally doable. Try staying at the Chatham Bars for that long. You'll have to take out a 2nd mortgage! ENJOY!

    Houses are not updated. There is mold throughout the house. Washer was broken. Oven didn't work…read more Owners didn't care.

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    Pilgrim Village - Living room

    Living room

    Pilgrim Village - 2nd pond

    2nd pond

    Pilgrim Village - View of beach

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    View of beach

    New England Vacation Rentals and Property Management - vacation_rentals - Updated July 2026

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