Cape Cod and Islands Vacation Rentals for Intimate Weddings in 2027

A Cape house, your favorite people, a backyard ceremony, and a whole weekend together by the water. There is so much to love about an intimate wedding at a vacation rental, especially when everyone can stay for breakfast the next morning.

If you’re searching for a Cape Cod Airbnb wedding, you’ll find options here on Vrbo, WeNeedaVacation, and owners’ websites, too. These houses and compounds have published wedding offerings, room for a substantial overnight group, and outdoor spaces worth getting excited about. Some are best for a tiny celebration; others welcome a larger guest list with a separate event agreement.

I’ve organized them by region, including Martha’s Vineyard, Nantucket, and one option just off Cape in Onset. Start with the guest counts below, then find the setting that feels like you.

Compare Cape Cod and Islands wedding rentals

The overnight limit and wedding guest limit are separate. Event figures below are published ceilings; your own celebration still needs approval. Ask whether children, the couple, and vendors count toward the total.

Swipe across to compare all details.

Property and booking link	Location	Overnight guests	Published wedding limit and conditions
Copper Beech House	Falmouth	Comfortably 18; confirm maximum	20 total attendees; advance approval
Waterfront Cape Cod Escape	West Yarmouth	Up to 26 advertised; confirm included buildings	50 attendees
Gentle Heritage waterfront mansion	Orleans	16+ on Airbnb; 9 bedrooms, 15 beds	Spring and fall after Labor Day; full week and separate wedding lease; confirm event capacity
Our Great Gatsby	Chatham	19	Directory lists 150; tents allowed; confirm plan
North Chatham two-house estate	North Chatham	20	80; prior approval; no music
The Dexter	Vineyard Haven, Martha’s Vineyard	18	30 attendees
Private Edgartown Estate	Edgartown, Martha’s Vineyard	16	99; advance event approval
Nantucket house and cottage	Nantucket	Up to 23 advertised	75; owner lease required
Nantucket Dreams	Tom Nevers, Nantucket	16	Directory lists 150; tents allowed; confirm plan
The Yard House	Onset, Wareham, just off Cape	Plan around 14; owner also advertises 16	Directory lists 50; no tents; discuss event with owner

The directory figures for Our Great Gatsby, Nantucket Dreams, and The Yard House come from WeNeedaVacation’s wedding listings. Confirm the current event agreement for your dates before reserving accommodation.

Can you have a wedding at a Cape Cod Airbnb or Vrbo?

It depends on the property and your plans. Airbnb’s Community Disturbance Policy prohibits disruptive and open-invitation gatherings, and hosts set their own event house rules. Vrbo also separates overnight occupancy from events and visitors. A wedding needs express permission, even if every guest is sleeping at the house.

For every property below, share your actual ceremony and reception plans and get written approval before booking. An event listing establishes that weddings are offered; the owner still needs to approve your guest count, vendors, music, and use of the grounds.

Upper Cape: a historic Falmouth house for a tiny wedding

Copper Beech House in Falmouth

Copper Beech has that classic Cape house feeling: historic shingles, a garden, and a big backyard for spending time together. The owner’s gallery describes outdoor dining, a bocce court, and a fire pit beneath the house’s namesake tree. It’s a lovely starting point for a relaxed celebration with your closest people.

The Vrbo listing describes nine bedrooms and comfortable sleeping for 18, although its headline advertises 20. Confirm the final overnight maximum when you inquire. Two kitchens and a large dining room are useful for the rest of the weekend.

Weddings require advance approval, possible additional fees, and no more than 20 total event attendees. That makes this a particularly small-wedding option. Ask which part of the yard is approved for your gathering and whether your proposed setup is permitted; tent permission is not published.

Mid Cape: a waterfront wedding weekend in West Yarmouth

Waterfront Cape Cod Escape on Lewis Bay

If you’re picturing a house overlooking the bay, Waterfront Cape Cod Escape deserves a look. The owner describes vintage Cape character, a landscaped backyard, porch and patio, panoramic Lewis Bay views, and a hot tub. The water gives the whole weekend a coastal backdrop, from getting ready to those last few portraits before dinner.

The listing advertises up to 26 overnight guests and explicitly permits weddings with up to 50 event attendees. Confirm exactly which buildings and bedrooms your reservation includes. The main-house and optional-cottage descriptions have conflicting room totals, so request the current sleeping plan before assigning beds.

This is an appealing option when you want more overnight room than most single houses provide. Ask the owner to identify the approved ceremony and dinner areas, including any tent arrangements and the indoor rain plan. A waterfront lawn still needs an event layout that works for your group.

Lower Cape: waterfront estates in Orleans and Chatham

Gentle Heritage: the waterfront mansion in Orleans

Buckle up, because this is still one of my favorites on the whole list. Gentle Heritage in Orleans, listed on Airbnb as “Waterfront. Private beach. Heated Pool.”, has the house, the lawn, and the water views that make you stop scrolling. The estate sits above Pleasant Bay with a private beach and a heated pool. It is such a beautiful setting for a wedding weekend with your closest people.

The Airbnb listing shows 16+ overnight guests, nine bedrooms, 15 beds, and 5.5 bathrooms. Confirm the exact overnight maximum and room arrangements with the host before assigning beds. The listing describes a quiet estate at the end of a private road, with plenty of places to spend time together between wedding plans.

The Airbnb host’s house rules explicitly allow weddings in spring and fall after Labor Day, with a full-week rental and a separate set of event rules and lease. Those rules describe wedding weeks running Wednesday to Wednesday, which differs from the ordinary Friday-to-Friday holiday rental. Ask for the 2027 wedding agreement, current pricing, approved event guest count, tent permission, and rain plan before booking. A standard accommodation reservation does not include wedding approval. Read the Airbnb house rules.

Our Great Gatsby in Chatham

Our Great Gatsby pairs a 1930s family estate with salt-marsh and Nantucket Sound views. Its 1.3-acre setting includes a manicured lawn, gardens, decks, and a veranda. Picture a garden ceremony followed by a long dinner, with the house as the backdrop for the weekend.

There are nine bedrooms, 3.5 bathrooms, and space for 19 overnight guests. The bed layout includes plenty of twins, so check how the rooms suit your families and friends. A large kitchen and a butler’s pantry with a second refrigerator help with group meals.

The owner explicitly advertises small weddings and rehearsal dinners. The platform’s wedding directory lists a 150-person event ceiling and allows tents; discuss a layout for your smaller guest list. Published minimums are two nights off-season and seven nights in summer. Confirm wedding-specific terms, parking, and event charges with the owner.

The North Chatham two-house estate

This North Chatham estate has an especially pretty outdoor setting: a large lawn, flower garden and gazebo, meadow, water views, and stairs to a private beach. Across 3.2 acres, a traditional main house and cottage provide 13 bedrooms, with a published overnight limit of 20.

Weddings are permitted for up to 80 attendees with prior approval and possible fees. The event rules specify no music. That is an important part of choosing this house: talk through your ceremony and dinner plans with the owner before you fall in love with the setting.

There is also no air conditioning, pets are not allowed, and the listing permits at most five children under 13. Those details make this a more particular fit for a quiet wedding weekend. Confirm the usable event area, wet-weather arrangements, and any tent permissions; the acreage alone does not establish an approved reception layout.

Martha’s Vineyard: a captain’s house or a private estate

The Dexter in Vineyard Haven

The Dexter is a renovated 1843 captain’s house in downtown Vineyard Haven, with nine bedrooms and sleeping space for 18. Individually decorated rooms and multiple lounges give a group places to spread out, while the wraparound porch, patio, and two decks bring everyone outside. The owner’s amenities page provides another look at the gathering spaces.

Its current Vrbo rules explicitly permit weddings and cap events at 30 attendees. This is an intimate downtown option with a yard, rather than a sprawling estate lawn. Discuss your proposed outdoor setup with the owner.

The house advertises four to six parking spaces, which makes transportation worth planning early. If you’re bringing your dog, the listing permits up to two pets; confirm the specific arrangements for your stay. A porch-centered weekend with your favorite people sounds pretty wonderful here.

Private Edgartown Estate

For more outdoor room, Private Edgartown Estate offers seven acres with fields, a fenced yard, a koi pond, pool, terraces, and an outdoor fireplace. The shingled house and garden setting offer plenty to build a relaxed wedding weekend around.

Seven bedrooms and 5.5 bathrooms accommodate 16 overnight guests, with a listed bed arrangement of kings and queens. Guests bring their own sheets and towels, so include that in your arrival plans.

The current rules explicitly allow weddings with advance event approval, up to a published maximum of 99 attendees. Ask the owner which lawns are available for your ceremony and dinner, whether a tent is permitted, and how a rainy day would work. Those details are not supplied by the acreage or event ceiling. Dogs are considered individually, so mention yours in the initial inquiry if you’d like them there.

Nantucket: house-and-cottage wedding stays

Nantucket house and cottage with a pool

This Nantucket compound combines a six-bedroom main house and two-bedroom cottage, with up to 23 overnight guests advertised. The sleeping arrangement includes a bunk room, so request the layout before deciding how comfortably it fits your group.

White oak, marble, and coastal furnishings give the interiors a polished feel. Outside, the heated pool and spa, stone terraces, covered porches, and gas fire pit create several places to gather throughout the weekend. It is especially appealing if you love a pool-and-patio setting.

The current rules allow weddings with up to 75 event attendees. An owner lease is required, and the minimum renter age is 30; pets are not allowed. Confirm the event areas and reception layout, including any tent plan. The listing places the compound in a residential neighborhood and does not establish a large tent lawn.

Nantucket Dreams in Tom Nevers

Nantucket Dreams has a five-bedroom main house and two-bedroom carriage house, with a stated overnight capacity of 16. Its three-acre setting, large yard, pool and spa, patio, and ocean-view decks make it a strong starting point for a wedding weekend outside. Pebble Beach is about 300 yards away.

The owner expressly advertises weddings. The wedding directory lists up to 150 event guests and permits tents. For an intimate celebration, ask where the owner recommends placing a smaller ceremony and dinner, along with catering access and a workable rain plan.

The house uses an upside-down layout, with living spaces above the bedrooms, so ask about stairs and access for anyone who needs them. Sunday-to-Sunday rentals are advertised, and pets are not permitted. Confirm the current wedding rental period and all event charges before booking.

Just off Cape: a backyard celebration in Onset

The Yard House in Onset, Wareham

Onset is just off Cape, and The Yard House offers a sweet alternative if you’re open to that location. The gray-shingled, porch-front house has a broad fenced yard, mature trees, outdoor seating, and a fire pit. Onset Beach is a block away.

The owner welcomes inquiries for small weddings and events. The WeNeedaVacation wedding directory lists 50 event guests and no tents, making an approved rain plan especially important.

There are six bedrooms, but the published sleeping figures differ: the owner advertises 16 while the rental description says 14. Plan around 14 until the owner confirms the current arrangement. Parking is limited to four driveway cars and seven vehicles overall. Discuss transport for any additional wedding guests as part of the event inquiry.

Planning your Cape Cod rental wedding

Start with your people and the actual floor plan

Choose two numbers before you inquire: everyone sleeping at the property, and everyone attending the wedding. Share both with the owner, along with your date ideas and the kind of celebration you want. Ask for the current bed layout, including bunks, shared rooms, cottage charges, and any limits involving children.

Then think through how your guests will move around the house and yard. Check stairs, bathroom access, and the distance between the gathering area and parking with anyone who has access needs. A bedroom total only tells you part of that story.

Give the yard and the rain plan equal attention

Ask where the ceremony, dinner, catering, toilets, and any approved tent can go. Request an event layout for your actual guest count. A garden, pool terrace, and lawn all create different possibilities, and the owner can explain which spaces are available for wedding use.

Make sure the wet-weather plan fits the entire celebration, including vendors and equipment. Confirm setup and cleanup times, music rules, power, parking, event fees, and any insurance or permits required for your specific plans. Get those details into the written event agreement before committing to the rental.

Leave room for the whole weekend

For a Vineyard or Nantucket wedding, build your travel plans around how guests and vendors will reach the island. Discuss equipment deliveries and transport with your team early. On the mainland, consider where day guests will park and whether a shuttle makes the day easier.

Compare the full cost of accommodation, the event, catering, rentals, and setup help. That gives you a useful wedding budget and helps you choose the house that fits the experience you want. If you’re also considering the mountains, my New Hampshire intimate wedding rental guide has more house-and-weekend ideas.

Photographing your intimate Cape Cod wedding

What I love about this kind of wedding is the time together: getting ready in a house full of your people, having a ceremony that feels personal, and staying for dinner under the evening sky. A beautiful setting is part of it, but the real story is what happens there with everyone you love.

If you’re planning an intimate Cape Cod or Islands wedding in 2027, tell me what you’re imagining. Share your guest count and the places you’re considering, and we can talk about photography for your wedding weekend.