Explore Observatory Hill Golf Retreats
Apartment
10.0Exceptional
(52 Reviews)
1 Bedroom
1 Bath
3 Guests
450 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $305/Night
7 Nights - US $2,135
House
- Boston
- ·
- Neighborhood Nine
- 0.31 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5 Guests
947.22 ft²
- Parking
View- Air Conditioner
Internet
US $238/Night
7 Nights - US $1,669
Hotel
9.6Exceptional
(1003 Reviews)
1 Bath
Breakfast- Parking
- Kitchen
- Air Conditioner
US $294/Night
7 Nights - US $2,059
House
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $428/Night
7 Nights - US $2,996
House
- Boston
- ·
- East Cambridge
- 0.19 mi to center
9.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1399.31 ft²
Oceanfront- Breakfast
EV Charge Station- Parking
US $700/Night
7 Nights - US $4,900
Apartment
- Boston
- ·
- Somerville
- 0.68 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $389/Night
7 Nights - US $2,721
Apartment
- Boston
- ·
- West Cambridge
- 0.29 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1175 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $456/Night
7 Nights - US $3,189
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $413/Night
7 Nights - US $2,888
Condo
- Boston
- ·
- Neighborhood Nine
- 0.31 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $347/Night
7 Nights - US $2,429
Luxury Places to Stay in Observatory Hill
Over 2089+ Luxury Places to Stay in or Near Observatory Hill
Apartment
- Boston
- ·
- Lower Allston
- 0.45 mi to center
8.9Fabulous
(36 Reviews)
14 Bedrooms
1 Bath
3 Guests
602.78 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $7,670/Night
7 Nights - US $53,690
Condo
- Boston
- ·
- Griggs Park
- 0.02 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
4 Baths
10 Guests
1001 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,730/Night
7 Nights - US $19,110
Apartment
- Boston
- ·
- East Cambridge
- 0.31 mi to center
9.4Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
7 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,272/Night
7 Nights - US $8,906
New
Apartment
- Boston
- ·
- Lower Allston
- 0.45 mi to center
2 Bedrooms
1 Bath
5 Guests
820 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,177/Night
7 Nights - US $8,237
New
House
6 Bedrooms
3 Baths
23 Guests
Hot Tub- Parking
- Balcony/Terrace
- Air Conditioner
US $1,172/Night
7 Nights - US $8,202
House
5 Bedrooms
4 Baths
10 Guests
3229.17 ft²
- Parking
- View
- Air Conditioner
- Internet
US $1,114/Night
7 Nights - US $7,801
US $1,009/Night
7 Nights - US $7,064
US $1,009/Night
7 Nights - US $7,064
US $1,002/Night
7 Nights - US $7,015
Top-Rated Villas with a Pool in Observatory Hill
Over 286+ Top-Rated Private Villas with a Pool in or Near Observatory Hill
House
10.0Exceptional
(15 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
Private Pool- Parking
Pool- Balcony/Terrace
US $787/Night
7 Nights - US $5,512
Hotel
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $287/Night
7 Nights - US $2,011
Bed & Breakfast
- Boston
- ·
- Oak Square
- 0.45 mi to center
9.6Exceptional
(75 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $172/Night
7 Nights - US $1,203
Hotel
9.2Exceptional
(1114 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $325/Night
7 Nights - US $2,274
Bed & Breakfast
- Boston
- ·
- Oak Square
- 0.38 mi to center
9.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
1 Guest
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $178/Night
7 Nights - US $1,247
Hotel
9.0Exceptional
(2 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $245/Night
7 Nights - US $1,712
Hotel
8.9Fabulous
(224 Reviews)
6 Baths
482.22 ft²
- Private Pool
- EV Charge Station
- Parking
- Pool
US $379/Night
7 Nights - US $2,652
Hotel
8.4Excellent
(1744 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $170/Night
7 Nights - US $1,188
US $1,002/Night
7 Nights - US $7,015
Pet-Friendly Villas in Observatory Hill
Over 915+ Pet-Friendly Private Villas in or Near Observatory Hill
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $479/Night
7 Nights - US $3,351
New
Apartment
- Boston
- ·
- Lower Allston
- 0.44 mi to center
2 Bedrooms
2 Baths
5 Guests
753.47 ft²
- Balcony/Terrace
- Air Conditioner
- Internet
- Pet Friendly
US $865/Night
7 Nights - US $6,053
Hotel
- Boston
- ·
- Lower Allston
- 0.47 mi to center
9.4Exceptional
(252 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $347/Night
7 Nights - US $2,426
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $526/Night
7 Nights - US $3,685
Apartment
2 Bedrooms
2 Baths
5 Guests
807.29 ft²
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
US $507/Night
7 Nights - US $3,548
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $450/Night
7 Nights - US $3,150
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $431/Night
7 Nights - US $3,019
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $413/Night
7 Nights - US $2,888
New
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $410/Night
7 Nights - US $2,872
Large Private Villas in Observatory Hill
Over 191+ Large Villas in or Near Observatory Hill for Groups and Families
House
- Boston
- ·
- North Cambridge
- 0.19 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $439/Night
7 Nights - US $3,070
Apartment
8.8Fabulous
(201 Reviews)
5 Bedrooms
3 Baths
10 Guests
706.83 ft²
- Parking
Skiing- Balcony/Terrace
- Air Conditioner
US $111/Night
7 Nights - US $777
Apartment
8.0Excellent
(2 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Kitchen
- Internet
- Child Friendly
Laundry
US $528/Night
7 Nights - US $3,698
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
3225 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $862/Night
7 Nights - US $6,034
House
- Boston
- ·
- Strawberry Hill
- 0.26 mi to center
8.5Fabulous
(69 Reviews)
16 Bedrooms
7 Baths
26 Guests
1013.6 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $59/Night
7 Nights - US $413
Apartment
- Boston
- ·
- Strawberry Hill
- 0.26 mi to center
9.6Exceptional
(45 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $655/Night
7 Nights - US $4,583
Condo
9.6Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $780/Night
7 Nights - US $5,460
House
11 Bedrooms
7 Baths
10 Guests
2150 ft²
- Oceanfront
- Parking
Ocean View- Balcony/Terrace
US $601/Night
7 Nights - US $4,206
Condo
- Boston
- ·
- Somerville
- 0.71 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
4 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,566/Night
7 Nights - US $10,962
Wheelchair Accessible Holiday Homes in Observatory Hill
Over 877+ Wheelchair Accessible Villas and Holiday Homes in or Near Observatory Hill
US $898/Night
7 Nights - US $6,284
Hotel
- Boston
- ·
- East Cambridge
- 0.24 mi to center
8.6Fabulous
(206 Reviews)
12 Baths
406.34 ft²
- Breakfast
- EV Charge Station
- Parking
- Balcony/Terrace
US $584/Night
7 Nights - US $4,088
Hotel
9.4Exceptional
(1008 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $288/Night
7 Nights - US $2,016
US $898/Night
7 Nights - US $6,284
Hotel
- Boston
- ·
- Lower Allston
- 0.30 mi to center
8.2Excellent
(1914 Reviews)
12 Baths
426.07 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $264/Night
7 Nights - US $1,846
US $502/Night
7 Nights - US $3,516
US $478/Night
7 Nights - US $3,345
US $478/Night
7 Nights - US $3,345
US $476/Night
7 Nights - US $3,329
Observatory Hill Villas, Airbnb and Holiday Homes Under $200
Over 519+ Observatory Hill Private Villas, Airbnb and Holiday Homes Under $200
Apartment
7.4Very Good
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $171/Night
7 Nights - US $1,200
Apartment
- Boston
- ·
- East Cambridge
- 0.40 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
13 Guests
9752.1 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $124/Night
7 Nights - US $868
Hotel
7.8Very Good
(1002 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $170/Night
7 Nights - US $1,191
House
- Boston
- ·
- North Cambridge
- 0.28 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1650 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $186/Night
7 Nights - US $1,302
Apartment
- Boston
- ·
- North Cambridge
- 0.65 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
8072.93 ft²
- Hot Tub
- Parking
- Internet
- Child Friendly
US $168/Night
7 Nights - US $1,173
Apartment
- Boston
- ·
- Aspinwall Hill
- 0.16 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $136/Night
7 Nights - US $951
Apartment
- Boston
- ·
- Coolidge Corner South Side
- 0.25 mi to center
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
450 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $139/Night
7 Nights - US $970
Apartment
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $161/Night
7 Nights - US $1,128
Apartment
- Boston
- ·
- North Brookline
- 0.35 mi to center
2 Bedrooms
1 Bath
4 Guests
734 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $189/Night
7 Nights - US $1,323
Instantly Bookable Villa Rentals in Observatory Hill
Over 1300+ Instantly Bookable Private Villas in or Near Observatory Hill
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $384/Night
7 Nights - US $2,687
US $146/Night
7 Nights - US $1,021
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $411/Night
7 Nights - US $2,880
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.42 mi to center
1 Bedroom
1 Bath
4 Guests
647 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $384/Night
7 Nights - US $2,687
US $455/Night
7 Nights - US $3,182
US $455/Night
7 Nights - US $3,182
US $417/Night
7 Nights - US $2,922
US $417/Night
7 Nights - US $2,922
Hotel
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $264/Night
7 Nights - US $1,849
Book a Last Minute Place to Stay in Observatory Hill
About Observatory Hill Vacation Rentals
Explore over 2098 golf accommodation rentals in Observatory Hill. From luxurious golf villas to cozy golf cabins, golf resorts, and exclusive golf hotels, each offers premium amenities designed for families, groups, and golf enthusiasts. Enjoy exceptional comfort and a one-of-a-kind golf experience with these incredible accommodations. Perfect for tranquil golf escapes, relaxing retreats, or golf-inspired getaways, these properties provide style and comfort in Observatory Hill.
Looking for last-minute deals or the best offers on golf villas, golf cabins, golf resorts, and other golf retreats? StayAndPlay makes it easy to compare options in Observatory Hill. Choose from spacious family-friendly stays, charming golf escapes, or luxurious golf retreats tailored for ultimate relaxation and play.
Find spacious family-friendly golf accommodations, golf cottage, or luxurious golf villas—all designed for maximum comfort and convenience during your visit.On average, golf accommodation rentals in Observatory Hill offer approximately 651.37 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning golf course surroundings.
The average nightly rate for golf accommodation rentals in Observatory Hill typically ranges around US $436.
StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Observatory Hill. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.
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Top Golf Accommodation Types in Observatory Hill
| Type | Count |
|---|---|
| Holiday Apartments | 1381 |
| Vacation Homes | 343 |
| B&B | 19 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Observatory Hill
★ Pro Tip: StayAndPlay simplifies your search for the best golf accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore golf villas, cozy golf cabins, golf hotels, and golf resorts. Filter by availability, pricing, cancellation options, and amenities to discover the ideal golf retreat in Observatory Hill.
Weather in Observatory Hill, MA
View the weather forecast for Observatory Hill before booking your Observatory Hill Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Observatory Hill?
What are the best golf resorts, luxury villas, and vacation rentals in Observatory Hill?
Looking for a place to stay in Observatory Hill? Explore these highly-rated golf vacation rentals for a one-of-a-kind golf retreat, where you can relax, unwind, and get ready to play your best game:
- NEW Modern Apartment Near Boston & Harvard Square.
- Remodeled Spacious Apartment in Perfect Location
- Funky and cozy home ! A little bit of everything for everyone.
- Beautiful Spacious 4BRM House!
- 1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts
- 1st FL Apt, in Somerville walk to Subways, Univ, Entertainment, & Restaurants
- 4BR/4BA | Parking + Chef’s Kitchen | Near BU/BC
- Sunsplashed Serenity - Walk to Harvard & Fresh Pond from a Huron Village Oasis
- Free Parking Sleeps 10 3BD 3BA Amenities Holiday Home
- Luxury 1BR: Sleek Kitchen + City Charm | Suite 2
How many golf stays with private pools are available in Observatory Hill?
Find exceptional golf retreats with private pools near Observatory Hill on StayAndPlay. Relax in serene golf vacation rentals with exclusive pool access and picturesque golf course views. Whether it's a spacious golf villa or a secluded golf cabin, these properties offer the perfect blend of luxury and relaxation, so you can focus on your game.
- Lux 2BR in Assembly Square | Pool & Fitness Center
- Well-located Kendall Sq 1BR w courtyard BOS-388
- Stylish 1BR in Assembly Square | Pool, Gym & Views
- Luxurious 2BR - 2BA Apt at Hyatus
What are the top-rated golf retreats in Observatory Hill for family stays?
Searching for a family-friendly golf retreat in Observatory Hill? Explore these top-rated options, each loved by families and groups who have stayed in Observatory Hill:
- Charming Condo, Quiet Neighborhood, Easy Access to Bos & Cambridge Via T or Car
- Historic Harvard & MIT Victorian
- The Charles Hotel
How many StayAndPlay golf vacation rentals are available in Observatory Hill?
StayAndPlay, as of 2026, features over 2098 unique golf villas, golf hotels, golf resorts, and more in Observatory Hill. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.
By 2026, StayAndPlay has curated over 2098 stunning properties in Observatory Hill, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 2098 premier golf accommodations in Observatory Hill. Find your ideal golf-retreat and play your best game with StayAndPlay.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| West Cambridge Golf Rental Cottages and Golf Getaways in Boston, Massachusetts | 1954 |
| Neighborhood Nine Golf Rental Cottages and Golf Getaways in Boston, Massachusetts | 1884 |
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