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5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach

Photo gallery for 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach

Main house on left, guest house on right
Exterior
View to outside living area and fireplace
living area, view towards dining & entry
living area

Reviews

10 out of 10
Exceptional
8 bedrooms6+ bathroomsSleeps 20

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Nantucket, MA
  • Place, Jetties Beach
    ‪18 min walk‬
  • Place, Nantucket Atheneum
    ‪3 min drive‬
  • Place, Nantucket Ferry Terminal
    ‪3 min drive‬
  • Airport, Nantucket, MA (ACK-Nantucket Memorial)
    ‪11 min drive‬

Rooms & beds

8 bedrooms (sleeps 20)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

+1
1 Queen Bed, 1 Twin Bed and 3 Child Beds

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed and 1 Child Bed

Bedroom 6

4 Child Beds

Guest House Bed 1

1 Queen Bed

Guest House Bed 2

2 Twin Beds

Media/Playroom

1 Double Futon

6 bathrooms, 2 half bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet · Jetted bathtub

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet

Bathroom 7

Bathtub or shower · Toilet

Bathroom 8

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Garden
Dining area

About this property

5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach

Newly updated & unequaled compared to other estate homes in the sought after Cliff area. "Pilgrim's Bliss" offers a unique combination of a large back yard for children to play (check carefully, as many large homes don't have this amenity), ample guest house that can sleep 4, salt water heated pool, a magical private flower lined path down to 2 Adirondack's at the edge of a pond frequented by geese, ducks, turtles, stunning white egrets and bullfrogs. All walking distance to town and beaches. Privacy from tall trees & hedges (in the rear there is no home for more than 100 ft) and having the benefit of being set back from, not on, Cliff Road (a main, busy artery to town with the associated noise and traffic). Pilgrim's Bliss is situated on almost 1/2 an acre, much larger than other vacation rental homes in the area. Always ask about lot size & beware of other new build, soulless spec homes, some on a tiny boxed in lot with overlooking neighbors & no privacy. Pilgrim's Bliss offers a calm, luxurious setting for extended, multi-generational families unparalleled in its expansive offering at the price. The main house has 6 bedrooms, there is the separate 2 bedroom guest house with covered terrace, the heated salt water pool, wrap around porch with an outdoor living room, outdoor fireplace and two distinct dining areas. There is also the large, idyllic flower filled back yard where children can play, or in the evening stroll down the winding path lined with Christmas lights to the pond and enjoy a glass of wine while looking at the star filled skies, amplified by Nantucket's position 25 miles out in the Atlantic. The Cliff district starts from town and runs parallel to Jetties & Galley beaches, beach clubs and restaurants. 'Pilgrim's Bliss' has consistently garnered extraordinary reviews from families and wedding parties. You're a 1 minute drive, 4 minute bike or 10 minute walk to the center of town, and a street away from the restaurants and tennis courts of the popular Westmoor Club. We offer an extensive range of books, a fully equipped children’s playroom, plasma TV's, Sonos internet music streaming & international radio feeds, steam room and air conditioning.

Note: July, August rentals must be Saturday to Saturday & are 7 day minimum
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Air conditioning
Outdoor Space

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House Rules

Check in after 3:30 PM
Minimum age to rent: 35
Check out before 9:30 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
House rules are outlined in the lease. There are separate swimming pool, fireplace and bbq rules.
Guests must remove sand by towel or outdoor shower before entering and shall not sit on any indoor furniture in wet clothing or swimsuit
Pool is not included Oct 1 to April 30th. During that time guest house is only available on request at added fee.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
Property Registration Number C0065071970

About the neighborhood

Nantucket

Nantucket Town, a neighborhood in Nantucket, is home to this vacation home. Lily Pond Park and Smith's Point Wildlife Sanctuary reflect the area's natural beauty and area attractions include Vestal St Observatory and Loines Observatory. Dreamland Film and Performing Arts Center and White Heron Theatre are also worth visiting. Kayaking and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
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Map
Nantucket, MA

What's nearby

  • Jetties Beach - 18 min walk - 1.5 km
  • Whaling Museum - 19 min walk - 1.7 km
  • Nantucket Atheneum - 3 min drive - 1.5 km
  • Nantucket Ferry Terminal - 3 min drive - 1.5 km
  • Children's Beach - 3 min drive - 1.5 km

Getting around

  • Nantucket, MA (ACK-Nantucket Memorial) - 9 min drive

Restaurants

  • ‪Brotherhood of Thieves - ‬19 min walk
  • ‪Lemon Press - ‬3 min drive
  • ‪The Rose and Crown - ‬3 min drive
  • ‪The Nantucket Tap Room - ‬18 min walk
  • ‪Stubbys - ‬3 min drive

Frequently asked questions

Does 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach?

As of Apr 19, 2026, prices found for a 1-night stay for 2 adults at 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach on Apr 28, 2026 start from $3,715, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach?

Check-in begins at 3:30 PM.

What time is check-out at 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach?

Check-out is at 9:30 AM.

Where is 5 star, grand 8 BR estate, large yard, pool, pond, walk to town & beach located?

Located in Nantucket Town, this vacation home is within a 15-minute walk of Lily Pond Park and Jethro Coffin House. First Congregational Church and Fire Hose Cart House are also within 1 mi (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 32 out of 33 reviews
Rating 8 - Good. 1 out of 33 reviews
Rating 6 - Okay. 0 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Janet S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful place!

Outstanding!
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Jillian G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ideal Nantucket Experience

I was looking at weeks to rebook for next year before I even left. This house is beautiful and was perfect for our family vacation. The kids loved that there was an actual yard to run around and a very manageable ~12 min walk to the Beach (my 5 year old twins did it without a problem). Everything was so clean and we felt very well taken care of during our stay.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Lawrence M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highly recommend

Very up to date. Spacious. Extremely well equipped kitchen. Very attractive property. We’ll worth the price.
Stayed 8 nights in Sep 2023
Verified

10/10 Excellent

Susan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful home for big family gatherings

We stayed at Pilgrim’s Bliss for one week in late September for my daughter’s wedding. Our family was able to spread out in the main house and the pool house and there was plenty of room for all. The house was wonderfully appointed with lots of beautiful decorating and many cozy touches. The kitchen was fully equipped and the common spaces were generous and comfortable. The caretaker was super responsive and she also recommended a service to stock our kitchen before arrival. All in all, an A+++ experience, we would definitely return!
Stayed 7 nights in Sep 2024
Verified

8/10 Good

Katherine K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful House and Location

We had a great time staying here with my family and a few friends to celebrate my 40th birthday! The house and yard are gorgeous and the location is perfect! We did have a problem with the heat/AC which made the pool house unsuitable to sleep in for the first 4 nights of our stay. It took management three days to fix the problem which was unfortunate as two of my guests decided to leave and checked into a hotel instead. Other than the heat/AC issue our stay was great and I would definitely come again!
Stayed 7 nights in Aug 2024
Archival

10/10 Excellent

Nathan O.

A little slice of heaven!

I've stayed in luxury properties all of the world and would recommend this home with a full 5 stars. Although only two of us stayed in the home, it could accommodate any large family with kids. The house is set for both kids to hangout and for adults to have adult time. But even with two people we were very comfortable. Robin is a joy to work with and is very attentive. The grounds are stunning and wonderfully cared for and the lake is a great place to unwind after the day. Location to town is excellent, a quick walk or short drive. A great home in ACK!
Verified

10/10 Excellent

Suzanne Z.

Just Like Home!

From the moment the moment we arrived at Pilgrim's Bliss we knew we were in for a grand 50th anniversary celebration with our family at this beautiful Nantucket home! It is so much more than the photos reveal and the amenities so much more than listed. The house was immaculate and the gardens and landscaping exceptional. All the descriptions were very helpful in our planning and furnishings and accessories are second to none. The home was just the right size for our family and best memories were making meals together in the wonderfully, equipped kitchen and laughing around a large dining room table. The grand back porch was a gathering place with a cup of coffee every morning as we planned the day and for toasting s'mores treats in the evening. The few needs we had were addressed in a blink of an eye by Amanda who made wonderful beach and dining recommendations for Jettie's Beach and The Sandbar our family favorites! Biking to Sconset with lunch at Claudette's, Bartlett's Farm, Cisco Brewers and a visit to The Whaling Museum were tops on our list. This home is so conveniently located to town, the Stop-N-Shop , and ice cream trips to the Juice Guys. Thank you for sharing your beautiful home with our family. None of our children or grandchildren had ever been to Nantucket before. We ALL loved" Pilgrim's Bliss"....and I think it loved us back! Upon departing we threw our pennies in at Brandt Point and would come back in a heartbeat! After my final communication with the owner I felt like I was saying goodbye to a kind friend. Thank you for your graciousness , Robin.
Verified

10/10 Excellent

Paula H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Nantucket Family Vacation

Loved this spacious and conveniently-located house!
Stayed 5 nights in May 2022
Verified

10/10 Excellent

Steve P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nantucket -2021

This is a perfect family house and cottage setup. My wife and I had our 3 married children and 7 grandchildren ( aged from 1 year old to 10) with us and there was plenty of room. In fact, there were 4 unused beds available! The house was comfortably furnished for the adults but it wasn’t so fancy as to cause us to worry about the kids harming anything.
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Anson G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a great house for all 18 of us. 2 weeks of what the house is named “Bliss” Pilgrim.

Well organized and property manager always on top of things. Beds were very comfortable. Some more firm which is great. Air conditioning super. Kitchen with 2 dish washers. 2 refrigs and freezers. Dinners around a great long table plus plenty of seating for the very large TV. Cloths wash and dryer 2 each top floor plus backup below. Definitely go again! Thanks Robin.
Stayed 14 nights in Jul 2021
Verified

10/10 Excellent

tim s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Experience

Excellent experience from start to finish. The house itself is terrific, well laid out, clean, top of the line finishes. The neighborhood is well located on the island and the property manager was very responsive to any and all questions. Would recommend to anyone.
Verified

10/10 Excellent

Barbara D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nantucket Bliss

We had a wonderful experience at Pilgrims Bliss. The house is perfect for a large family and Robin and Amanda were very accommodating to our needs.The grounds are beautiful with lots of space for kids to explore and play. Just what we all needed in a time that is so uncertain. Happy memories for all!
Verified

10/10 Excellent

Ann F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and property

Pilgrim’s Bliss is a lovely, clean and beautifully decorated home with everything needed to have a stress free vacation. The kids loved the heated pool and the bunk beds, the adults loved the porches, fireplaces and the big bedrooms and baths. It made our family vacation (15 of us - ages 3months to grandparents) one of the best we have had. The owner, Robin, and the on island manager Amanda are very responsive and easy to work with.
Verified

10/10 Excellent

Wendy E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Bliss in Pilgrim!

Our extended family came out to Nantucket for a family gathering. Robin the owner was incredibly helpful prior to our arrival and during our stay when we had some issues with the Sonos. All were addressed and solved promptly. It was windy and chilly so we had the fire going non stop. The large and warm open space made for perfect family time. Our son, an Executive Head Chef in NYC, loved cooking for us in the professionally outfitted kitchen. The location was perfect. Quiet area but close enough to walk to town. We will be back next fall!!
Stayed 4 nights in Oct 2019
Verified

10/10 Excellent

Jeff A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

Robin was super easy to work with. The home surpassed our expectations immensely. We had 20 family members there for.a family wedding. The bedrooms are huge and private and elegant for all our needs. The home is well stocked with kitchen, bathroom and pantry supplies. The pool house was equally amazing. The yard is beautiful. The pool was inviting albeit mid September is cool in Nantucket. The house is perfectly located. We walked to the Westmoor club where the rehearsal dinner was. It was an easy uber ride to Mary’s Church and we could have walked except for the formal gowns and black ties. Amanda was great to us and the house was ready and waiting for our arrival. Robin was easy to work with and helped me with all the VRBO concerns I had with a late booking. I highly recommend this home for any large family gathering. It was so easy to entertain there. Thank you Robin and Amanda.
Stayed 3 nights in Sep 2019
Verified

10/10 Excellent

Herb H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home for large family (or two)

This home was perfect for our two families. The teenagers were able to hang out in the basement or pool house when desired, and everyone gathered around the pool and spacious decks in the afternoon. The open indoor layout (kitchen-dining-family room) was also great in the mornings and evenings. A wonderful house.
From a partner site

10/10 Excellent

JOSEPH K.

Absolutely Amazing!!!

Absolutely Amazing Home! It doesn’t get much nicer than this home. It just felt like home from the moment we walked through the front door. Open living space created a great area for conversation and togetherness. The owner, Robin, was super accommodating and helpful. He treated us like family. We spent 3 nights here for an adult friend’s retreat and will definitely be back every year. Wonderfully furnished to feel like you are home. The Outside Property created an immediate sense of peace and relaxation..........from the outdoor covered porch, fire place conversation area to the Adirondack Chairs down at the lake.........both perfect places to unwind with a good book. The heated Pool was icing on the cake. The location was a short 10-12 minute walk to Town. Amazing, Amazing, Amazing and Highly recommended........we will be back for sure. Thank you Robin!!!
Stayed 3 nights in May 2018
Archival

10/10 Excellent

Bill F.

Great place for our family reunion

We had a great time in ACK and loved our time at Pilgrim's Bliss. It worked great for the four days we had the whole family there. The pool was the highlight and the deck space was fabulous for our dinners. We had a couple catered dinners and rented some tables and chairs which worked great. The easy walk to Steps Beach proved manageable even for my 87 year old mother and the Juice Bar was also well within range. My wife and I walked everyday, a few mornings down to Eel Point Rd and Dionis Beach (yesterday morning in a very steady rain!) and one morning took the group out to loop Smith Point. That was a highlight. Lots of great memories for all
Archival

10/10 Excellent

Allison W.

Beautiful Property, Perfect Location

Thanks so much for providing your beautiful home for us to stay on beautiful Nantucket! We were here to celebrate our matriarch's 70th birthday and, young and old, everyone had a wonderful time. We hated to leave! So many nice memories. Pilgrim's Bliss is perfect.
Archival

10/10 Excellent

Sarah M.

Amazing Family Vacation Oasis

Our extended family of 16 stayed at the "Pilgrim Bliss" house over July 4th week, and "bliss" it was. Only minutes away from the beach and town, we had endless options of how to spend out warm summer days. Nights at Pilgrim Bliss were spent huddled around the campfire, lounging out on the beautiful wrap-around porch, overlooking the backyard and pool. It was such a great way to spend our holiday. The house came fully equipped with everything we needed to make this July 4th perfect at our home away from home. Thank you Pilgrim Bliss for helping us make family memories for life!
Archival

10/10 Excellent

Melissa B.

Perfection on Nantucket

Pilgrim's Bliss is aptly named . . . the home is impeccable yet comfortable, close to town yet serene, spacious yet warm . . . we couldn't have asked for more! I rented the home for a group of 12 women and we were impressed with everything from the decor to the landscaping to the enviably outfitted kitchen! Our group so loved the back deck fireplace, and we spent hours chatting and visiting in this beautiful space. The beds were incredibly comfortable, the showers luxurious and the proximity to Steps beach and Something Natural made for easy and fun walking excursions for sandwiches and sunshine . . . so perfectly Nantucket! Working with the owner was a dream, and we can't wait to book this piece of heaven again. We had high expectations going in, and they were surpassed. Well done!
Archival

10/10 Excellent

Patricia S.

Gorgeous Property ideally located!

This is a gorgeous manicured property, located about a mile from Nantucket village and about 1/2 mile to Stepps beach which was ideal for my young grandchildren. The House was spotlessly clean, spacious, with beautiful architectural details and all the amenities of home. Each bedroom had a very large bathroom for optimum privacy. We loved the attached guest house which was just as charming as the main house. Sitting by the pool in the evening provided a nice way to wind down after a busy day of touring, biking, swimming. When we dined in, it was always on the large outdoor porch that accommodated our 14 family members. Fun to be all together! We loved the local bakery, "Something Natural" which was a short walk or bike ride away-delicious home made breads and pastries, plus sandwiches for lunch. A safe bike path was right across the street from Pilgrim Rd, so we felt very comfortable allowing the children to ride. Nearby Barlett Farms provided us with delicious fresh produce and cheeses. I guess I can just sum this up by saying this property is on the top of the list of our favorite annual family vacations. From 8 to 80 years old, there was something for everyone to do and enjoy.
Archival

10/10 Excellent

Betina W.

Terrific, Wonderful, Magical...

What a terrific, wonderful, magical place this is! We had a suberb stay and already can't wait to come back! So many blissful new memories for our family - our youngest son lost his first tooth here!! Thanks for the hospitality and the beautiful vacation setting!
Archival

10/10 Excellent

D S.

ACK Christmas Stroll

This was our first trip to Nantucket for Christmas Stroll & our first time at Pilgrim's Bliss. What a wonderful experience. The house made you feel like you had come home the minute you walked in the door. Every convenience & amenity was thought of (my personal favorite was the bathrobes!!). An absolutely magical experience. We would love to come back again.
Archival

10/10 Excellent

D M.

We are rarely at a loss for words

We are rarely at a loss for words, but... here are two: THANK YOU. Bliss, indeed, also relaxing, warm and elegant come to mind. The greatest gift a family can share is time together. Thank you for letting our family share time in your wonderful home! We particularly love the exotic wooden chair (at the front door) and all the interesting art. "Pilgrims Bliss" is aptly named. With deepest appreciation

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