Boutique Hotels in Oak Bluffs

Escape and exhale in this bright, airy 3-bedroom, 2.5-bathroom retreat that sleeps up to 7. Peaceful and centrally located between Oak Bluffs and Vineyard Haven, near bike paths, field preserves and hiking trails. Easy access to the Lagoon for swimming, sailing and sunbathing; near Farm Neck Golf Club, the popular Featherstone community arts center and the MV “Y.” This home has an open, well-stocked cook's kitchen (gas stove) and inviting dining room. A welcoming living room with cozy sitting room/library and convenient half-bath complete the first floor. The upper floor has a generous primary en-suite and two guest bedrooms with a shared bath. A/C and ceiling fans for hot summer days. The large private yard is beautifully landscaped with an expansive back deck for summer entertaining and the quintessential screened porch for morning coffee and relaxing with family and friends. This home is nestled in a quiet community in a private association that is a short drive to downtown Oak Bluffs and central to all down-island hot spots and beaches.Well-appointed with comfortable, contemporary furnishings and updated kitchen and baths. Bikes and beach chairs available for use. Linens including beach towels provided. Available for rentals through the year.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No commercial photos or videos on the property..Trash will be picked up on Mondays and Thursdays. Please use the containers on the property, and make sure the lids are securely closed.,The fireplace is decorative and is not to be used for any reason..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Located in Oak Bluffs, enjoy what this 2-bedroom apartment has to offer. With a washing machine, WiFi, AC, iron, hair dryer, and heating, this wonderful and enjoyable property provides all the comforts you need. The bathroom is equipped with everything you'll need for a comfortable stay. Kickback, relax, and enjoy everything Oak Bluffs and our apartment has to offer.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Nestled in the charming town of East Chop, this 3-bedroom vacation home offers the perfect escape for your next getaway. As you arrive, you'll be greeted by the cozy porch, inviting you to sit back, relax, and soak in the peaceful surroundings. Inside, you'll find a fully stocked kitchen, complete with a stove, oven, refrigerator, and all the necessary appliances to whip up delicious meals. Gather around the dining table and enjoy quality time with your loved ones. When it's time to unwind, retreat to the comfortable living room and catch up on your favorite shows on the smart TV with satellite/cable channels.Just a short 16-minute walk away, you can explore the vibrant Oak Bluffs Harbor, or hop in the car for a 3-minute drive to the Oak Bluffs Ferry Terminal and Oak Bluffs Town Beach. Enjoy the convenience of having a washing machine and dryer, as well as free WiFi, to make your stay even more comfortable.Whether you're looking to relax on the beach, enjoy outdoor activities, or simply spend quality time with family and friends, this vacation home has everything you need for an unforgettable getaway.About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Come stay at our quaint Victorian cottage overlooking downtown Oak Bluffs and the Harbor, which are just a few blocks away within easy walking distance. The cottage sits on the edge of a large park bordering the aptly named Sunset Lake, so it's like having an extra-large front yard for games of frisbee or flying kites. There's a few public beaches within walking distance (just over a half mile), or you can drive to them or anywhere on the island in minutes. The house is not fancy, but it has everything you need to make it home base for your island adventure. The fabled Cottage City cottages are just across the park, as is the Oak Bluffs main street and nightlife.About pets:Pets allowed: dogs and cats (limit 2 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Please remove all sheets from beds used, and towels, and put on the washer before leaving..Please wash all dishes before leaving..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell.There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.MASTER BEDROOMKing size bed with gel infused memory form Serta iComfort mattress, down pillows. One hundred year old antique trunk from India at the foot of the bed. Above the bed are 24' beams reclaimed from a Zipper factory in Brooklyn NY. Skylight above bed, black out shades and 60" TV with Apple TV. Climate control with central AC and fan.Super comfy leather chair, walk-in closet with full bathroom.QUEEN BEDROOMQueen size bed on the second floor with central heating and window AC. There is office desk with chair. Also two big closets and half bath.KITCHENFully stocked kitchen with toaster oven, microwave, coffee maker, wine rack and five seat counter stool. DINING AREACustom walnut slab dining table with eight seats. There is custom built-in bench seat with Maroccan cactus silk pillows for four people, four Indonesian wicker chairs and Turkish antique rug.SCREENED PORCHThis outdoor space is perfect for breakfasts or barbecue. There is a large sofa in the corner and table seating for six people. OUTDOOR AREASThe entire outdoor space is covered by leland cypress trees so you have 100% privacy.- big porch with massive sofa what you can use for sunbathing or watching the stars and stainless steel grill;- eight person hot tub- outdoor bathroom what you can use before and after a hot tub to not entry the house with three shower heads, sink and toilet; - outdoor fireplace with teak adirondack chairs and endless firewood;- round hanging daybed for two people - wonderful place to read a book or just sit and listen to the birds;- two sun loungers.There is a washer and dryer in the basement. We do allow some pets which are allowed upon request.Pet policy: One pet maximum. No pets are allowed on the sofa, beds or on any of the furniture. You must bring your own dog bed as you are not allowed to use our blankets for them to sleep on. You must bring your own dog bowls. You must pick up all of your dog poop in the yard and do not let them pee in the house. Dogs must be supervised at all times and are not allowed to dig up the garden. Our cleaners charge an additional 100$ pet fee. Any damage to our home is your responsibility. If your dog does any damage to our home we will be going threw VRBO claims to immediately resolve the issues.About pets:Pets allowed: dogs (limit 1 total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.

Location!!! Location!!! This updated cottage is a quick walk to town, beach, Tony’s Deli, tennis and basketball courts, and so much more. Relax on the wrap around porch , enjoy the outdoor shower after a walk back from the beach, warm up near the fire pit while BBQ is on the grill. Walk to all downtown Oak Bluffs attractions. All new beds and furniture. Bring your fav sheets and bath towels to complete your comfort (Or rent locally on the island). Flexible work week. Work space for telecommuters. About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:must supply their own sheets and towels.No objects on the grass. Can burn out grass.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.

Renovated in 2022, The Panola House is tucked away on a private lot with its own roundabout driveway. Walk to the center of Oak Bluffs and the OB Ferry. (Scenic 15 minute walk brings you to the Historic Campground, right behind the center of Downtown OB, Circuit Avenue .) Inkwell Beach is a short 5-10 minute walk from there, if you don’t stop for ice cream :) Each location above is accessible by bike in 7 minutes and car in less than 10 minutes. The 1st floor has 1,500 sq. ft of living space with an additional 1,500 in the finished lower level, perfect for family time, children, teenagers and adults. There is a 65 inch TV that connects to Sling TV for cable and Netflix. (Media & entertainment, board games, and movies.).The lower level also has a pullout full-sized bed and a 1/2 bathroom in addition to the three bedrooms on the 1st floor. Central A/C throughout the house (installed in 2022). The outdoor landscape/ grounds, front and rear decks, are surrounded by beautiful gardens and trees which provide tranquility and privacy. There is a gas outdoor grill on the rear deck and outdoor shower. We have welcomed families as 5-Star VRBO hosts since 2013 and would like to share our new family home with wonderful families and great guests.Please message me if you have a question or if there is any information we can provide. Best regards,Jason About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Enjoy one of Oak Bluffs’ newest accommodations perched at the peak of the Highlands boasting just a 10 minute walk to town center and beaches. This home just completed a full (100%) renovation of its original 1900 build that has transformed everything from all rooms & living spaces along with associated appliances & fixtures, landscaping and outdoor amenities.This fully renovated property boasts all new accommodations including: OUTDOORS- Wraparound porch with seating to enjoy views of the private yard or to observe passersby from the front of the house- Semicircular drive with private parking for 2 vehicles and access to a dedicated EV/Tesla charger- Private patio with hot tub, lounge seating, outdoor dinning and grill area- Rear lawn with fire pit, space for games and fun - Outdoor shower to use upon returning from the beach FIRST FLOOR- You will be greeted by an open 1st floor plan with living, kitchen and dining areas- Features include wood floors throughout, independent AC, wolf & sub-zero appliances, French doors opening to the porch and patio - Rear of the home hosts a large pantry, mudroom rear-entry, half bath and complete laundry room SECOND FLOOR- Includes 3 bedrooms with raised vaulted ceilings and a bonus sunroom space, all with independent AC (mini splits) units- Two full baths with specialty features including a shared hall bath with spa-like wet room, Kohler fixtures and large soaker tub- Second bath is ensuite to the primary bedroom and has shower massage jets; and skylight windows adorn both bedroom & bath- Three balconies off of two bedrooms and the sunroom provide seating space and views over looking three different directions of the homeSLEEPING ARRANGEMENTSIt will sleep up to 8 people. - Primary bedroom has a queen (2)- Second bedroom has a queen (2)- Third bedroom has a queen bed (2)- Sunroom can also sleep (2)Guests can use all parts of the home except the basement and 2 hall closets on the second floor that are for cleaning crew supplies and owner storage.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

This Oak Bluffs home boasts 3 inviting bedrooms and a cozy loft, including 2 king beds, 2 full beds and a queen sofa bed. With 4 bathrooms equipped with amenities like a hair dryer and shower, guests will feel right at home. The pleasant living room space also provides a cozy soft bed, an excellent spot to unwind after a day of exploring. With speakers on every level ask Alexa a question or play your favorite tune. This is a stylish modern NEW CONSTRUCTION home. A 3 minute drive or a leisurely 10 minute walk to town. And a 20 min walk to Inkwell beach. This home is my home. Make it your home during your stay. Book now and enjoy everything this brand new house has to offer.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.